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2026-07-14T06:20:12Z
User contributions
MediaWiki 1.43.8
https://chemwiki.ch.ic.ac.uk/index.php?title=Grubbs%27_Catalyst&diff=13992
Grubbs' Catalyst
2007-12-07T14:30:17Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} |Grubbs' Catalyst, 1st Generation<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:1st_grubbs.jpg|thumb|center|200|1st_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | 3D shape - |[[Image:grubbscat1st.png|thumb|center|200|1st_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | Jmol<jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>grubbs.mol<br />
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120126 0 0 0 1 V2000<br />
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M END<br />
<br />
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</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>43</sub>H<sub>72</sub>C<sub>12</sub>P<sub>2</sub>Ru<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 822.96g/mol<br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 172222-30-9<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 153 °C (dec.)<br />
|-<br />
| Appearance<br />
| Purple Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
Grubb's Catalyst is a transition metal carbene complex. It was first synthesised by Rober H. Grubbs and it was named after him. There are two generations of the catalyst. Grubbs' Catalyst is very versitile as, unlike other olefin metathesis catalysts, it tolerates other functional groups in the alkene and is compatible with many solvents. <ref>#</ref><br />
<br />
<br />
==The First Generation Grubb’s Catalyst==<br />
The 1st generation Grubbs’ Catalyst is used in olefin cross-metathesis, ring-opening metathesis polymerization (ROMP) and ring-closing metathesis. Grubb’s Catalyst is widely used in organic synthesis as it is useful because it is a stable compound in air. <ref>#</ref><br />
<br />
===Olefin Metathesis===<br />
[[Image:Metathesis.png|thumb|left|200|Metathesis]]Olefin metathesis is a reaction between two alkene molecules. Olefin metathesis involves redistribution of alkene bonds. The groups bonded to the carbon atoms of the double bond are exchanged between molecules, resulting in two new alkene molecules with swapped groups. The general scope is outlined by the diagram on the left. <ref>#</ref><br />
<br />
==The Second Generation Catalyst ==<br />
The Second Generation Catalyst is also widely used in organic synthesis. In the second generation catalyst the phosphine is replaced with a cyclic bis-amino carbene ligand. It is easily synthesised by combining the first generation catalyst and alkoxy-protected 1,2-dimesityl-4,5-dihydroimidazol-2-ylidene. The resulting ruthenium is coordinated to two carbine groups. The second generation catalyst has a higher activity than the first one does and it is also a air-stable compound. <ref>#</ref><br />
<br />
==Application==<br />
One of the application of Grubbs’ Catalyst is in aerospace industry. A spaceship has to be made of very strong material, but microcracks form over time. A new material for spaceship hulls contains Grubbs’ Catalyst and capsules of dicyclopentadiene. When a crack forms in the hull, the Grubbs’ Catalyst polymerizes dicyclopentadiene and seals the crack. This is possible as dicyclopentadiene can undergo ring opening metathesis polymerisation.<ref>#</ref><br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Grubbs'_catalyst<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/579726<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/569747<br />
# http://www.3dchem.com/molecules.asp?ID=208#<br />
<br />
<noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} |Grubbs' Catalyst, 2nd Generation<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:2nd_grubbs.jpg|thumb|center|200|2nd_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | 3D shape |-[[Image:grubbscata2nd.jpg|thumb|center|200|2nd_Grubbs'Catalyst]]<br />
|-<br />
! {{chembox header}} | General<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>46</sub>H<sub>65</sub>C<sub>12</sub>N<sub>2</sub>PRu<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 848.97g/mol<br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 246047-72-3<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 143.5-148.5 °C<br />
|-<br />
| Appearance<br />
| Pinkish-Brown Solid<br />
|-<br />
<br />
<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=Grubbs%27_Catalyst&diff=13988
Grubbs' Catalyst
2007-12-07T14:22:11Z
<p>Sh606: /* Application */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} |Grubbs' Catalyst, 1st Generation<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:1st_grubbs.jpg|thumb|center|200|1st_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | 3D shape - |[[Image:grubbscat1st.png|thumb|center|200|1st_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | Jmol<jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>200</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>grubbs.mol<br />
<br />
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120126 0 0 0 1 V2000<br />
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4.5249 -1.5444 -4.0806 C 0 0 0 0 0<br />
4.1281 -0.3363 -3.2120 C 0 0 0 0 0<br />
0.2619 -0.1566 0.0750 Ru 0 0 0 0 0<br />
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M END<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>43</sub>H<sub>72</sub>C<sub>12</sub>P<sub>2</sub>Ru<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 822.96g/mol<br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 172222-30-9<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 153 °C (dec.)<br />
|-<br />
| Appearance<br />
| Purple Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
Grubb's Catalyst is a transition metal carbene complex. It was first synthesised by Rober H. Grubbs and it was named after him. There are two generations of the catalyst. Grubbs' Catalyst is very versitile as, unlike other olefin metathesis catalysts, it tolerates other functional groups in the alkene and is compatible with many solvents. <ref>#</ref><br />
<br />
==The First Generation Grubb’s Catalyst==<br />
The 1st generation Grubbs’ Catalyst is used in olefin cross-metathesis, ring-opening metathesis polymerization (ROMP) and ring-closing metathesis. Grubb’s Catalyst is widely used in organic synthesis as it is useful because it is a stable compound in air. <ref>#</ref><br />
<br />
===Olefin Metathesis===<br />
[[Image:Metathesis.png|thumb|left|200|Metathesis]]Olefin metathesis is a reaction between two alkene molecules. Olefin metathesis involves redistribution of alkene bonds. The groups bonded to the carbon atoms of the double bond are exchanged between molecules, resulting in two new alkene molecules with swapped groups. The general scope is outlined by the diagram on the left. <ref>#</ref><br />
<br />
==The Second Generation Catalyst ==<br />
The Second Generation Catalyst is also widely used in organic synthesis. It is easily synthesised by combining the first generation catalyst and alkoxy-protected 1,2-dimesityl-4,5-dihydroimidazol-2-ylidene. The resulting ruthenium is coordinated to two carbine groups. The second generation catalyst has a higher activity than the first one does and it is also a air-stable compound. <ref>#</ref><br />
<br />
==Application==<br />
One of the application of Grubbs’ Catalyst is in aerospace industry. A spaceship has to be made of very strong material, but microcracks form over time. A new material for spaceship hulls contains Grubbs’ Catalyst and capsules of dicyclopentadiene. When a crack forms in the hull, the Grubbs’ Catalyst polymerizes dicyclopentadiene and seals the crack. This is possible as dicyclopentadiene can undergo ring opening metathesis polymerisation.<ref>#</ref><br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Grubbs'_catalyst<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/579726<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/569747<br />
# http://www.3dchem.com/molecules.asp?ID=208#<br />
<br />
<noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} |Grubbs' Catalyst, 2nd Generation<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:2nd_grubbs.jpg|thumb|center|200|2nd_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | 3D shape |-[[Image:grubbscata2nd.jpg|thumb|center|200|2nd_Grubbs'Catalyst]]<br />
|-<br />
! {{chembox header}} | General<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>46</sub>H<sub>65</sub>C<sub>12</sub>N<sub>2</sub>PRu<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 848.97g/mol<br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 246047-72-3<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 143.5-148.5 °C<br />
|-<br />
| Appearance<br />
| Pinkish-Brown Solid<br />
|-<br />
<br />
<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=Grubbs%27_Catalyst&diff=13987
Grubbs' Catalyst
2007-12-07T14:21:18Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} |Grubbs' Catalyst, 1st Generation<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:1st_grubbs.jpg|thumb|center|200|1st_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | 3D shape - |[[Image:grubbscat1st.png|thumb|center|200|1st_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | Jmol<jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
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-0.7343 -4.2777 2.1787 H 0 0 0 0 0<br />
-0.7084 -4.0917 0.4123 H 0 0 0 0 0<br />
-2.0037 1.2105 -0.3202 H 0 0 0 0 0<br />
-3.6987 1.4865 -1.7905 H 0 0 0 0 0<br />
-4.7459 1.1121 -3.9635 H 0 0 0 0 0<br />
-3.6530 -0.3466 -5.6814 H 0 0 0 0 0<br />
-1.4455 -1.4128 -5.1891 H 0 0 0 0 0<br />
-0.3346 -1.0696 -3.0758 H 0 0 0 0 0<br />
1 2 1 6 0 0<br />
1 8 1 1 0 0<br />
1 14 1 6 0 0<br />
1 20 1 1 0 0<br />
2 3 1 6 0 0<br />
2 7 1 0 0 0<br />
2 49 1 0 0 0<br />
3 4 1 6 0 0<br />
3 50 1 6 0 0<br />
3 51 1 0 0 0<br />
4 5 1 0 0 0<br />
4 52 1 6 0 0<br />
4 53 1 0 0 0<br />
5 6 1 1 0 0<br />
5 54 1 6 0 0<br />
5 55 1 0 0 0<br />
6 7 1 1 0 0<br />
6 56 1 0 0 0<br />
6 57 1 0 0 0<br />
7 58 1 0 0 0<br />
7 59 1 1 0 0<br />
8 9 1 1 0 0<br />
8 13 1 0 0 0<br />
8 60 1 6 0 0<br />
9 10 1 0 0 0<br />
9 61 1 1 0 0<br />
9 62 1 0 0 0<br />
10 11 1 0 0 0<br />
10 63 1 6 0 0<br />
10 64 1 1 0 0<br />
11 12 1 6 0 0<br />
11 65 1 0 0 0<br />
11 66 1 1 0 0<br />
12 13 1 0 0 0<br />
12 67 1 0 0 0<br />
12 68 1 6 0 0<br />
13 69 1 6 0 0<br />
13 70 1 1 0 0<br />
14 15 1 1 0 0<br />
14 19 1 6 0 0<br />
14 71 1 6 0 0<br />
15 16 1 6 0 0<br />
15 72 1 1 0 0<br />
15 73 1 0 0 0<br />
16 17 1 6 0 0<br />
16 74 1 0 0 0<br />
16 75 1 1 0 0<br />
17 18 1 6 0 0<br />
17 76 1 6 0 0<br />
17 77 1 0 0 0<br />
18 19 1 1 0 0<br />
18 78 1 6 0 0<br />
18 79 1 6 0 0<br />
19 80 1 1 0 0<br />
19 81 1 6 0 0<br />
20 21 1 1 0 0<br />
20 40 1 6 0 0<br />
20 41 1 1 0 0<br />
20 42 1 0 0 0<br />
21 22 1 1 0 0<br />
21 28 1 1 0 0<br />
21 34 1 0 0 0<br />
22 23 1 0 0 0<br />
22 27 1 1 0 0<br />
22 82 1 1 0 0<br />
23 24 1 0 0 0<br />
23 83 1 6 0 0<br />
23 84 1 1 0 0<br />
24 25 1 1 0 0<br />
24 85 1 6 0 0<br />
24 86 1 0 0 0<br />
25 26 1 0 0 0<br />
25 87 1 0 0 0<br />
25 88 1 1 0 0<br />
26 27 1 0 0 0<br />
26 89 1 6 0 0<br />
26 90 1 1 0 0<br />
27 91 1 1 0 0<br />
27 92 1 0 0 0<br />
28 29 1 0 0 0<br />
28 33 1 1 0 0<br />
28 93 1 6 0 0<br />
29 30 1 1 0 0<br />
29 94 1 1 0 0<br />
29 95 1 6 0 0<br />
30 31 1 1 0 0<br />
30 96 1 0 0 0<br />
30 97 1 6 0 0<br />
31 32 1 0 0 0<br />
31 98 1 1 0 0<br />
31 99 1 1 0 0<br />
32 33 1 6 0 0<br />
32100 1 1 0 0<br />
32101 1 6 0 0<br />
33102 1 0 0 0<br />
33103 1 1 0 0<br />
34 35 1 6 0 0<br />
34 39 1 0 0 0<br />
34104 1 1 0 0<br />
35 36 1 0 0 0<br />
35105 1 0 0 0<br />
35106 1 6 0 0<br />
36 37 1 0 0 0<br />
36107 1 6 0 0<br />
36108 1 1 0 0<br />
37 38 1 1 0 0<br />
37109 1 0 0 0<br />
37110 1 6 0 0<br />
38 39 1 0 0 0<br />
38111 1 0 0 0<br />
38112 1 1 0 0<br />
39113 1 1 0 0<br />
39114 1 6 0 0<br />
40 43 1 6 0 0<br />
40115 1 1 0 0<br />
43 44 2 0 0 0<br />
43 48 1 6 0 0<br />
44 45 1 6 0 0<br />
44116 1 1 0 0<br />
45 46 2 0 0 0<br />
45117 1 0 0 0<br />
46 47 1 0 0 0<br />
46118 1 6 0 0<br />
47 48 2 0 0 0<br />
47119 1 6 0 0<br />
48120 1 0 0 0<br />
M END<br />
<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>43</sub>H<sub>72</sub>C<sub>12</sub>P<sub>2</sub>Ru<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 822.96g/mol<br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 172222-30-9<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 153 °C (dec.)<br />
|-<br />
| Appearance<br />
| Purple Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
Grubb's Catalyst is a transition metal carbene complex. It was first synthesised by Rober H. Grubbs and it was named after him. There are two generations of the catalyst. Grubbs' Catalyst is very versitile as, unlike other olefin metathesis catalysts, it tolerates other functional groups in the alkene and is compatible with many solvents. <ref>#</ref><br />
<br />
==The First Generation Grubb’s Catalyst==<br />
The 1st generation Grubbs’ Catalyst is used in olefin cross-metathesis, ring-opening metathesis polymerization (ROMP) and ring-closing metathesis. Grubb’s Catalyst is widely used in organic synthesis as it is useful because it is a stable compound in air. <ref>#</ref><br />
<br />
===Olefin Metathesis===<br />
[[Image:Metathesis.png|thumb|left|200|Metathesis]]Olefin metathesis is a reaction between two alkene molecules. Olefin metathesis involves redistribution of alkene bonds. The groups bonded to the carbon atoms of the double bond are exchanged between molecules, resulting in two new alkene molecules with swapped groups. The general scope is outlined by the diagram on the left. <ref>#</ref><br />
<br />
==The Second Generation Catalyst ==<br />
The Second Generation Catalyst is also widely used in organic synthesis. It is easily synthesised by combining the first generation catalyst and alkoxy-protected 1,2-dimesityl-4,5-dihydroimidazol-2-ylidene. The resulting ruthenium is coordinated to two carbine groups. The second generation catalyst has a higher activity than the first one does and it is also a air-stable compound. <ref>#</ref><br />
<br />
==Application==<br />
One of the application of Grubbs’ Catalyst is in aerospace industry. A spaceship has to be made of very strong material, but microcracks form over time. A new material for spaceship hulls contains Grubbs’ Catalyst and capsules of dicyclopentadiene. When a crack forms in the hull, the Grubbs’ Catalyst polymerizes dicyclopentadiene and seals the crack. This is possible as dicyclopentadiene can undergo ring opening metathesis polymerisation.<br />
<ref>#</ref><br />
==References==<br />
# http://en.wikipedia.org/wiki/Grubbs'_catalyst<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/579726<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/569747<br />
# http://www.3dchem.com/molecules.asp?ID=208#<br />
<br />
<noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} |Grubbs' Catalyst, 2nd Generation<br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:2nd_grubbs.jpg|thumb|center|200|2nd_Grubbs' Catalyst]] <br />
|-<br />
! {{chembox header}} | 3D shape |-[[Image:grubbscata2nd.jpg|thumb|center|200|2nd_Grubbs'Catalyst]]<br />
|-<br />
! {{chembox header}} | General<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>46</sub>H<sub>65</sub>C<sub>12</sub>N<sub>2</sub>PRu<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 848.97g/mol<br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 246047-72-3<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 143.5-148.5 °C<br />
|-<br />
| Appearance<br />
| Pinkish-Brown Solid<br />
|-<br />
<br />
<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13985
It07:Schwartz
2007-12-07T14:16:29Z
<p>Sh606: /* Uses */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<ref>#</ref><br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes.<br />
<ref>#</ref><br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. <ref>#</ref>[[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz's Reagent<ref>#</ref>|700x850px]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13984
It07:Schwartz
2007-12-07T14:16:20Z
<p>Sh606: /* Schwartz reagent */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<ref>#</ref><br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. <ref>#</ref>[[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz's Reagent<ref>#</ref>|700x850px]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13983
It07:Schwartz
2007-12-07T14:15:56Z
<p>Sh606: /* Hydrozirconation reaction */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. <ref>#</ref>[[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz's Reagent<ref>#</ref>|700x850px]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13982
It07:Schwartz
2007-12-07T14:15:30Z
<p>Sh606: /* IR spectrum */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz's Reagent<ref>#</ref>|700x850px]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13980
It07:Schwartz
2007-12-07T14:15:08Z
<p>Sh606: /* IR spectrum */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz's Reagent<ref>#</ref>]]|700x850px<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13979
It07:Schwartz
2007-12-07T14:14:49Z
<p>Sh606: /* IR spectrum */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz|700x850px<ref>#</ref>]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13978
It07:Schwartz
2007-12-07T14:13:59Z
<p>Sh606: /* Schwartz reagent */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is very sensitive to air, moisture, and moderately sensitive to light sensitive. Therefore, it should be stored in the dark, dry place.<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz|700x850px]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=13975
It07:Schwartz
2007-12-07T14:12:52Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is an air, moisture, and moderately light sensitive compound. Therefore, it should be stored in the dark, dry place.<br />
<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation|700x850px]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz|700x850px]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13966
It07:wilkinson
2007-12-07T14:00:40Z
<p>Sh606: /* Comparison */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>270</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
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5 6 1 1 0 0<br />
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6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson<ref>#</ref>== <br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>|400x200px]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<ref># </ref><br />
<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O <br />
<br />
<br />
<br><br><br><br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
====Ilustration of Catalytic Chemistry <ref>#</ref>====<br />
[["http://www.chem.ox.ac.uk/shockwave/hydrogenation.html"]]<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison|400x300px]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in faster reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous.<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13965
It07:wilkinson
2007-12-07T13:58:36Z
<p>Sh606: /* Synthesis */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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! {{chembox header}} | 3D shape <jmol><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
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43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
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</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson<ref>#</ref>== <br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>|400x200px]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<ref># </ref><br />
<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O <br />
<br />
<br />
<br><br><br><br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
====Ilustration of Catalytic Chemistry <ref>#</ref>====<br />
[["http://www.chem.ox.ac.uk/shockwave/hydrogenation.html"]]<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison|400x300px]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13964
It07:wilkinson
2007-12-07T13:58:06Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
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1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
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3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
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-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
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-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
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4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
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6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
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5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
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0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
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0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
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-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
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1 41 1 0 0 0<br />
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44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
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59104 1 0 0 0<br />
M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson<ref>#</ref>== <br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>|400x200px]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent. <br />
<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O <br />
<br />
<br />
<br><br><br><br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
====Ilustration of Catalytic Chemistry <ref>#</ref>====<br />
[["http://www.chem.ox.ac.uk/shockwave/hydrogenation.html"]]<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison|400x300px]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13963
It07:wilkinson
2007-12-07T13:57:37Z
<p>Sh606: /* History of Geoffrey Wilkinson */</p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson== <ref>#</ref><br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>|400x200px]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent. <br />
<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O <br />
<br />
<br />
<br><br><br><br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
====Ilustration of Catalytic Chemistry <ref>#</ref>====<br />
[["http://www.chem.ox.ac.uk/shockwave/hydrogenation.html"]]<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison|400x300px]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13835
It07:wilkinson
2007-12-07T11:51:35Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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! {{chembox header}} | 3D shape <jmol><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
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M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>|400x200px]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent. <br />
<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O <br />
<br />
<br />
<br><br><br><br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
====Ilustration of Catalytic Chemistry <ref>#</ref>====<br />
[["http://www.chem.ox.ac.uk/shockwave/hydrogenation.html"]]<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison|400x300px]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
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<br />
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<br />
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<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
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<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13833
It07:wilkinson
2007-12-07T11:47:29Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
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2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
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3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
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-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
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-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
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4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
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1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
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3 60 1 0 0 0<br />
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6 7 2 0 0 0<br />
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7 64 1 1 0 0<br />
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8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
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10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
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14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
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16 17 2 0 0 0<br />
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17 18 1 1 0 0<br />
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18 19 2 0 0 0<br />
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21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
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25 26 2 0 0 0<br />
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27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
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29 30 2 0 0 0<br />
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30 31 1 6 0 0<br />
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31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
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38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
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44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
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M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>|400x200px]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent. <br />
<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O <br />
<br />
<br><br><br><br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison|400x300px]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
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<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13804
It07:wilkinson
2007-12-07T11:33:29Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
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0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
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0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
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3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
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1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
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1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
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0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
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4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
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4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
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-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
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28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13802
It07:wilkinson
2007-12-07T11:32:55Z
<p>Sh606: /* Applications */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>270</size><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<ref>#</ref><br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13798
It07:wilkinson
2007-12-07T11:31:56Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
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|<jmolApplet><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
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1 39 1 0 0 0<br />
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1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
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8 20 1 0 0 0<br />
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10 11 2 0 0 0<br />
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14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
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16 17 2 0 0 0<br />
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18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
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30 31 1 6 0 0<br />
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31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
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37 38 2 0 0 0<br />
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38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
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43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
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58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html<br />
# www.chemie.de/lexikon/e/Wilkinson's_catalyst</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13797
It07:wilkinson
2007-12-07T11:30:22Z
<p>Sh606: /* Synthesis */</p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
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104112 0 0 0 1 V2000<br />
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0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
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2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
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3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
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2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
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0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
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0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
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55 56 1 1 0 0<br />
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56 57 2 0 0 0<br />
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M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons<ref>#</ref>]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13794
It07:wilkinson
2007-12-07T11:29:45Z
<p>Sh606: /* History of Geoffrey Wilkinson */</p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
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6 7 2 0 0 0<br />
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7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson <ref>#</ref>]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13793
It07:wilkinson
2007-12-07T11:29:16Z
<p>Sh606: /* History of Geoffrey Wilkinson */</p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
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14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13792
It07:wilkinson
2007-12-07T11:28:41Z
<p>Sh606: /* Wilkinson's Catalyst */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#2</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
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<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13791
It07:wilkinson
2007-12-07T11:28:18Z
<p>Sh606: /* Wilkinson's Catalyst */</p>
<hr />
<div><noinclude><br />
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3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
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30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref>#1</ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13790
It07:wilkinson
2007-12-07T11:27:55Z
<p>Sh606: /* Wilkinson's Catalyst */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>270</size><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
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13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<ref></ref>Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13788
It07:wilkinson
2007-12-07T11:26:38Z
<p>Sh606: /* History of Geoffrey Wilkinson */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
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5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
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38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
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43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
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</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton. At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13787
It07:wilkinson
2007-12-07T11:26:07Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<inlineContents>wilkinsoncat.mol<br />
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104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
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2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
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3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
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-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
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-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
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4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
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0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
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2 7 1 0 0 0<br />
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3 4 1 6 0 0<br />
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8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
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10 11 2 0 0 0<br />
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11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
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14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
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18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
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21 22 2 0 0 0<br />
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21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
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24 25 1 1 0 0<br />
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27 32 1 0 0 0<br />
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32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
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33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
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41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
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44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
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47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 - 26 September 1996) was a British inorganic chemist, who shared the Nobel Prize for Chemistry (1973) with Ernst Fischer. Their pioneering work was in the chemistry of the organometallic. The work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
<br />
Wilkinson studied at Imperial College with a Royal Scholarship and graduated in 1941. After his study, Wilkinson worked with Atomic Energy Project in Canada (1943-1946). He held numerous posts in North America; University of California at Berkeley (1946-50), Massachusetts Institute of Technology (1950-51, Harvard University (1951-56). He returned to Imperial College and was appointed to the chair of Inorganic Chemistry in June 1955 and became a professor in 1988. Wilkinson was knighted in 1976. He also co-wrote a text book called Advanced Inorganic Chemistry (1962) with F. A. Cotton). At Imperial he worked on the complexes of transition metals. <br />
<br />
An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound Wilkinson and his partner were investigating was called ferrocene which has a single iron atom sandwiched between two five-sided carbon rings; later on, there were many other variations created with oher metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
One of his chemical discoveries was named after him, Wilkinson's Catalyst. This is an organometallic compound which activates small organic molecules so that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
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<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
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<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
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==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
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==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
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<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
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==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
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==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=13778
It07:wilkinson
2007-12-07T11:17:31Z
<p>Sh606: </p>
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<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
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<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt<br />
# http://nobelprize.org/nobel_prizes/chemistry/laureates/1973/wilkinson-autobio.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12872
It07:wilkinson
2007-12-04T15:56:55Z
<p>Sh606: /* Wilkinson's Catalyst */</p>
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<inlineContents>wilkinsoncat.mol<br />
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104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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|-<br />
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|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
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<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
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==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
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==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
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==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
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==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
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<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12871
It07:wilkinson
2007-12-04T15:55:31Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
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<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036<br />
# Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G.; Journal of the Chemical Society A, 1966, pp. 1711 - 1732, DOI: 10.1039/J19660001711<br />
# direktinfo.com/cmu/material/Presentations/Wilkinson%20Catalysis.ppt</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12870
It07:wilkinson
2007-12-04T15:54:23Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
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1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
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-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
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32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12869
It07:wilkinson
2007-12-04T15:53:58Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>270</size><br />
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
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-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
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5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
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11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12868
It07:wilkinson
2007-12-04T15:53:37Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
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|<jmolApplet><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
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</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12867
It07:wilkinson
2007-12-04T15:53:11Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
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4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
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2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
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1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
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8 13 1 1 0 0<br />
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10 11 2 0 0 0<br />
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11 12 1 1 0 0<br />
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14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
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21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
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27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
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30 31 1 6 0 0<br />
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31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
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38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
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44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
As shown in the tabulated data, Wilkinson catalyst is more active, resulting in fater reactions. Another advantage of Wilkinsons' Catalyst is that it can either be homogeneous or heterogeneous. <br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Comparison.jpg&diff=12865
File:Comparison.jpg
2007-12-04T15:50:11Z
<p>Sh606: </p>
<hr />
<div></div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12864
It07:wilkinson
2007-12-04T15:49:56Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
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<size>270</size><br />
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
==Comparison==<br />
[[Image:comparison.jpg|thumb|left|200|comparison]]<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12861
It07:wilkinson
2007-12-04T15:47:08Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>270</size><br />
<color>white</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
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4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
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-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
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-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
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4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
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2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
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4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
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10 11 2 0 0 0<br />
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11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
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21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
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23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
==Applications==<br />
Wilkinson's catalyst catalyzes the hydrogenation of alkenes. The reaction involves the initial dissociation of one or two triphenylphosphine ligands to give 14- or 12-electron complexes, respectively. It is then followed by oxidative addition of H<sub>2</sub> to the metal. <br />
Subsequent π-complexation of alkene, intramolecular hydride transfer, and reductive elimination then results in extrusion of the alkane product. <br />
<br />
Other applications of Wilkinson’s catalyst include: catalytic hydroboration of alkenes and the selective 1,4-reduction of α, β-unsaturated carbonyl compounds in concert with triethylsilane.<br />
<br />
<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
<br />
<br />
<br />
<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12856
It07:wilkinson
2007-12-04T15:42:03Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
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|-<br />
|<jmolApplet><br />
<size>270</size><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh<sub>3</sub>)<sub>3</sub>Cl.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Wilcatsyn.jpg&diff=12855
File:Wilcatsyn.jpg
2007-12-04T15:40:33Z
<p>Sh606: </p>
<hr />
<div></div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12854
It07:wilkinson
2007-12-04T15:40:22Z
<p>Sh606: /* Synthesis */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
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</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<br />
<br />
==Synthesis==<br />
[[Image:wilcatsyn.jpg|thumb|left|200|wilkinsons]]The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12853
It07:wilkinson
2007-12-04T15:38:04Z
<p>Sh606: /* Synthesis */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
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<size>270</size><br />
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<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<br />
<br />
==Synthesis==<br />
The Wilkinson's Catalyst is a square planar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl<sub>3</sub>(H<sub>2</sub>O)<sub>3</sub> + CH<sub>3</sub>CH<sub>2</sub>OH + 3 PPh<sub>3</sub> → RhCl(PPh<sub>3</sub>)<sub>3</sub> + CH<sub>3</sub>CHO + 2 HCl + 3 H<sub>2</sub>O<br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12852
It07:wilkinson
2007-12-04T15:36:18Z
<p>Sh606: /* Wilkinson's Catalyst */</p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
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|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Wilkinson's-catalyst_3D_balls.png|thumb|center|200|3DBall]] <br />
|-<br />
! {{chembox header}} | 3D shape <jmol><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff"<br />
|-<br />
|<jmolApplet><br />
<size>270</size><br />
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<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>wilkinsoncat.mol<br />
<br />
<br />
104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
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9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
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11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
</inlineContents><br />
</jmolApplet><br />
</jmol><br />
|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. Its use was popularlised by organometallic chemist, Sir Geoffrey Wilkinson (1973 Nobel Laureate) and it was named afer him.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<br />
<br />
==Synthesis==<br />
The Wilkinson's Catalyst is a square plaar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 → RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O <br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<color>black</color><br />
<script>zoom 80; cpk on;frame 1; move 10 -20 10 0 0 0 0 0 3; delay 1;</script><br />
<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:wilkinson&diff=12848
It07:wilkinson
2007-12-04T15:29:59Z
<p>Sh606: /* Wilkinson's Catalyst */</p>
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104112 0 0 0 1 V2000<br />
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0<br />
1.1431 1.9689 -3.0329 C 0 0 0 0 0<br />
0.5202 1.6759 -4.2514 C 0 0 0 0 0<br />
0.0553 2.6804 -5.1025 C 0 0 0 0 0<br />
0.2381 4.0214 -4.7685 C 0 0 0 0 0<br />
0.8850 4.3392 -3.5753 C 0 0 0 0 0<br />
1.3168 3.3241 -2.7189 C 0 0 0 0 0<br />
3.2256 1.6612 -1.1825 C 0 0 0 0 0<br />
4.2895 2.0906 -1.9837 C 0 0 0 0 0<br />
5.3078 2.8854 -1.4532 C 0 0 0 0 0<br />
5.2415 3.3147 -0.1271 C 0 0 0 0 0<br />
4.1415 2.9626 0.6556 C 0 0 0 0 0<br />
3.1433 2.1422 0.1273 C 0 0 0 0 0<br />
2.5553 -0.6693 -2.9837 C 0 0 0 0 0<br />
1.7496 -1.4378 -3.8325 C 0 0 0 0 0<br />
2.2861 -2.4006 -4.6897 C 0 0 0 0 0<br />
3.6580 -2.6491 -4.6887 C 0 0 0 0 0<br />
4.4770 -1.9229 -3.8252 C 0 0 0 0 0<br />
3.9271 -0.9472 -2.9908 C 0 0 0 0 0<br />
1.8066 0.6402 -1.8755 P 0 3 0 0 0<br />
2.4895 -3.0116 -0.7006 C 0 0 0 0 0<br />
1.4692 -3.3726 -1.5868 C 0 0 0 0 0<br />
1.6312 -4.4478 -2.4627 C 0 0 0 0 0<br />
2.8163 -5.1844 -2.4521 C 0 0 0 0 0<br />
3.8158 -4.8684 -1.5308 C 0 0 0 0 0<br />
3.6375 -3.8077 -0.6402 C 0 0 0 0 0<br />
1.6930 -2.8219 1.9100 C 0 0 0 0 0<br />
2.4316 -2.9296 3.0942 C 0 0 0 0 0<br />
2.0614 -3.8291 4.0967 C 0 0 0 0 0<br />
0.9548 -4.6600 3.9209 C 0 0 0 0 0<br />
0.2341 -4.5961 2.7283 C 0 0 0 0 0<br />
0.6105 -3.6936 1.7315 C 0 0 0 0 0<br />
3.7082 -0.8006 1.1206 C 0 0 0 0 0<br />
4.9447 -0.9029 0.4774 C 0 0 0 0 0<br />
6.0713 -0.2464 0.9766 C 0 0 0 0 0<br />
5.9780 0.5179 2.1402 C 0 0 0 0 0<br />
4.7485 0.6342 2.7897 C 0 0 0 0 0<br />
3.6218 -0.0078 2.2721 C 0 0 0 0 0<br />
2.1677 -1.6384 0.5153 P 0 3 0 0 0<br />
-0.8050 -0.9240 1.5944 Cl 0 0 0 0 0<br />
-1.2673 1.3055 -0.7138 P 0 3 0 0 0<br />
-1.9600 0.9997 -2.4063 C 0 0 0 0 0<br />
-2.8510 1.8725 -3.0379 C 0 0 0 0 0<br />
-3.3692 1.5738 -4.2997 C 0 0 0 0 0<br />
-3.0491 0.3654 -4.9203 C 0 0 0 0 0<br />
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0<br />
-1.7160 -0.2435 -2.9988 C 0 0 0 0 0<br />
-0.7810 3.0491 -0.3062 C 0 0 0 0 0<br />
-0.1187 3.2408 0.9128 C 0 0 0 0 0<br />
0.2956 4.5106 1.3177 C 0 0 0 0 0<br />
0.0355 5.6176 0.5096 C 0 0 0 0 0<br />
-0.6485 5.4438 -0.6940 C 0 0 0 0 0<br />
-1.0576 4.1696 -1.0938 C 0 0 0 0 0<br />
-2.8463 1.0234 0.2603 C 0 0 0 0 0<br />
-3.5530 -0.1726 0.0865 C 0 0 0 0 0<br />
-4.7370 -0.4120 0.7866 C 0 0 0 0 0<br />
-5.2370 0.5519 1.6631 C 0 0 0 0 0<br />
-4.5463 1.7523 1.8348 C 0 0 0 0 0<br />
-3.3593 1.9856 1.1369 C 0 0 0 0 0<br />
0.3800 0.6415 -4.5854 H 0 0 0 0 0<br />
-0.4429 2.4148 -6.0491 H 0 0 0 0 0<br />
-0.1140 4.8185 -5.4421 H 0 0 0 0 0<br />
1.0451 5.3954 -3.3036 H 0 0 0 0 0<br />
1.8069 3.6360 -1.7841 H 0 0 0 0 0<br />
4.3314 1.8231 -3.0516 H 0 0 0 0 0<br />
6.1490 3.2015 -2.0911 H 0 0 0 0 0<br />
6.0335 3.9578 0.2887 H 0 0 0 0 0<br />
4.0574 3.3374 1.6885 H 0 0 0 0 0<br />
2.2746 1.8922 0.7534 H 0 0 0 0 0<br />
0.6584 -1.3179 -3.8324 H 0 0 0 0 0<br />
1.6220 -2.9883 -5.3441 H 0 0 0 0 0<br />
4.0844 -3.4247 -5.3442 H 0 0 0 0 0<br />
5.5606 -2.1234 -3.7998 H 0 0 0 0 0<br />
4.6167 -0.4073 -2.3293 H 0 0 0 0 0<br />
0.5148 -2.8211 -1.5913 H 0 0 0 0 0<br />
0.8200 -4.7186 -3.1578 H 0 0 0 0 0<br />
2.9459 -6.0336 -3.1421 H 0 0 0 0 0<br />
4.7305 -5.4811 -1.4819 H 0 0 0 0 0<br />
4.4065 -3.6300 0.1274 H 0 0 0 0 0<br />
3.3326 -2.3235 3.2645 H 0 0 0 0 0<br />
2.6540 -3.8952 5.0239 H 0 0 0 0 0<br />
0.6662 -5.3756 4.7074 H 0 0 0 0 0<br />
-0.6272 -5.2652 2.5700 H 0 0 0 0 0<br />
0.0300 -3.6842 0.7953 H 0 0 0 0 0<br />
5.0569 -1.5000 -0.4374 H 0 0 0 0 0<br />
7.0365 -0.3324 0.4516 H 0 0 0 0 0<br />
6.8657 1.0364 2.5360 H 0 0 0 0 0<br />
4.6632 1.2478 3.7011 H 0 0 0 0 0<br />
2.6569 0.1188 2.7908 H 0 0 0 0 0<br />
-3.1849 2.7955 -2.5425 H 0 0 0 0 0<br />
-4.0593 2.2779 -4.7924 H 0 0 0 0 0<br />
-3.4716 0.1205 -5.9078 H 0 0 0 0 0<br />
-2.0239 -1.5340 -4.7144 H 0 0 0 0 0<br />
-1.1149 -0.9986 -2.4682 H 0 0 0 0 0<br />
0.0849 2.3852 1.5776 H 0 0 0 0 0<br />
0.8246 4.6387 2.2757 H 0 0 0 0 0<br />
0.3629 6.6219 0.8221 H 0 0 0 0 0<br />
-0.8555 6.3149 -1.3365 H 0 0 0 0 0<br />
-1.5785 4.0746 -2.0551 H 0 0 0 0 0<br />
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0<br />
-5.2797 -1.3605 0.6443 H 0 0 0 0 0<br />
-6.1750 0.3688 2.2115 H 0 0 0 0 0<br />
-4.9429 2.5200 2.5189 H 0 0 0 0 0<br />
-2.8474 2.9476 1.2892 H 0 0 0 0 0<br />
1 20 1 6 0 0<br />
1 39 1 0 0 0<br />
1 40 1 1 0 0<br />
1 41 1 0 0 0<br />
2 3 2 0 0 0<br />
2 7 1 0 0 0<br />
2 20 1 1 0 0<br />
3 4 1 6 0 0<br />
3 60 1 0 0 0<br />
4 5 2 0 0 0<br />
4 61 1 6 0 0<br />
5 6 1 1 0 0<br />
5 62 1 6 0 0<br />
6 7 2 0 0 0<br />
6 63 1 0 0 0<br />
7 64 1 1 0 0<br />
8 9 2 0 0 0<br />
8 13 1 1 0 0<br />
8 20 1 0 0 0<br />
9 10 1 0 0 0<br />
9 65 1 6 0 0<br />
10 11 2 0 0 0<br />
10 66 1 6 0 0<br />
11 12 1 1 0 0<br />
11 67 1 0 0 0<br />
12 13 2 0 0 0<br />
12 68 1 1 0 0<br />
13 69 1 1 0 0<br />
14 15 2 0 0 0<br />
14 19 1 0 0 0<br />
14 20 1 1 0 0<br />
15 16 1 6 0 0<br />
15 70 1 0 0 0<br />
16 17 2 0 0 0<br />
16 71 1 6 0 0<br />
17 18 1 1 0 0<br />
17 72 1 6 0 0<br />
18 19 2 0 0 0<br />
18 73 1 0 0 0<br />
19 74 1 1 0 0<br />
21 22 2 0 0 0<br />
21 26 1 0 0 0<br />
21 39 1 1 0 0<br />
22 23 1 6 0 0<br />
22 75 1 0 0 0<br />
23 24 2 0 0 0<br />
23 76 1 6 0 0<br />
24 25 1 1 0 0<br />
24 77 1 6 0 0<br />
25 26 2 0 0 0<br />
25 78 1 0 0 0<br />
26 79 1 1 0 0<br />
27 28 2 0 0 0<br />
27 32 1 0 0 0<br />
27 39 1 6 0 0<br />
28 29 1 1 0 0<br />
28 80 1 0 0 0<br />
29 30 2 0 0 0<br />
29 81 1 1 0 0<br />
30 31 1 6 0 0<br />
30 82 1 1 0 0<br />
31 32 2 0 0 0<br />
31 83 1 0 0 0<br />
32 84 1 6 0 0<br />
33 34 2 0 0 0<br />
33 38 1 1 0 0<br />
33 39 1 0 0 0<br />
34 35 1 0 0 0<br />
34 85 1 6 0 0<br />
35 36 2 0 0 0<br />
35 86 1 6 0 0<br />
36 37 1 1 0 0<br />
36 87 1 0 0 0<br />
37 38 2 0 0 0<br />
37 88 1 1 0 0<br />
38 89 1 1 0 0<br />
41 42 1 6 0 0<br />
41 48 1 0 0 0<br />
41 54 1 1 0 0<br />
42 43 2 0 0 0<br />
42 47 1 0 0 0<br />
43 44 1 6 0 0<br />
43 90 1 1 0 0<br />
44 45 2 0 0 0<br />
44 91 1 0 0 0<br />
45 46 1 1 0 0<br />
45 92 1 6 0 0<br />
46 47 2 0 0 0<br />
46 93 1 0 0 0<br />
47 94 1 1 0 0<br />
48 49 2 0 0 0<br />
48 53 1 6 0 0<br />
49 50 1 0 0 0<br />
49 95 1 1 0 0<br />
50 51 2 0 0 0<br />
50 96 1 1 0 0<br />
51 52 1 6 0 0<br />
51 97 1 0 0 0<br />
52 53 2 0 0 0<br />
52 98 1 6 0 0<br />
53 99 1 6 0 0<br />
54 55 2 0 0 0<br />
54 59 1 1 0 0<br />
55 56 1 1 0 0<br />
55100 1 6 0 0<br />
56 57 2 0 0 0<br />
56101 1 0 0 0<br />
57 58 1 0 0 0<br />
57102 1 1 0 0<br />
58 59 2 0 0 0<br />
58103 1 1 0 0<br />
59104 1 0 0 0<br />
M END<br />
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|-<br />
<br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| chlorotris(triphenylphosphine)rhodium(I)<br />
<br />
|-<br />
| Other names<br />
| Rhodium(I) tris-<br />
(triphenylphosphine) chloride,<br />
Wilkinson’s catalyst,<br />
Tris(triphenylphosphine)-<br />
rhodium chloride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 925.22 g/mol<sup>-1</sup><br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 14694-95-2<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| [http://en.wikipedia.org/wiki/Melting_point Melting point]<br />
| 245-250 °C<!-- (mention any decomposition) --><br />
|-<br />
|Appearance<br />
|Red Crystalline Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
<br />
== Wilkinson's Catalyst ==<br />
<br />
Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).<br />
It is a chemical compound with the formula RhCl(PPh<sub>3</sub>)<sub>3</sub>, where Ph represents phenyl group. It is named after the late organometallic chemist and 1973 Nobel Laureate, Sir Geoffrey Wilkinson who popularlized its use.<br />
<br />
==History of Geoffrey Wilkinson==<br />
[[Image:wilkinson.jpg|thumb|left|200|Wilkinson]] Sir Geoffrey Wilkinson (14 July 1921 -- 26 September 1996) was an English inorganic chemist who shared the Nobel Prize for Chemistry in 1973 for his pioneering work on the organometallic compounds of the transition metals. Wilkinson was born near Manchester and he obtained a Royal Scholarship for study at Imperial College, London, from where he graduated in 1941. He held numerous posts in North America, and was assistant professor at Harvard 1951-56. <br />
<br />
In June 1955 he was appointed to the chair of Inorganic Chemistry at Imperial College in the University of London, and from then on worked almost entirely on the complexes of transition metals. He cowrote the textbook Advanced Inorganic Chemistry (1962).<br />
<br />
Wilkinson's Nobel-prize-winning work was done with US chemist R B Woodward. An organometallic molecule consists of a metal atom sandwiched between carbon rings. The synthetic compound they were investigating, ferrocene, turned out to have a single iron atom sandwiched between two five-sided carbon rings; materials were later created with other metals and four-, six-, seven-, and eight-membered carbon rings.<br />
<br />
His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.<br />
One of his chemical discoveries earned his name, Wilkinson's Catalyst. This organometallic compound activates small organic molecules such that the bond-breaking and bond-formation pathways are readily accessible.<br />
<br />
Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.<br />
<br />
==Synthesis==<br />
The Wilkinson's Catalyst is a square plaar, 16-electron complex. It is usually synthesised by a reaction of rhodium trichloride with triphenylphosphine. This synthesis is conducted in refluxing ethanol, which serves as the reducing agent.<br />
RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 → RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O <br />
<br />
==spectrum==<br />
<br />
13C NMR<br />
[[Image:NMR.jpg]]<br />
<br />
1H NMR<br />
[[Image:H-NMR.jpg]]<br />
<br />
Infra red<br />
[[Image:Infra-red.jpg]]<br />
<br />
MS<br />
[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]<br />
<br />
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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1<br />
TITLE NONE 2<br />
AUTHOR WWW daemon apache NONE 3<br />
REVDAT 1 19-Nov-07 0 NONE 4<br />
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0<br />
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0<br />
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0<br />
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0<br />
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0<br />
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0<br />
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0<br />
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0<br />
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0<br />
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0<br />
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0<br />
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0<br />
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0<br />
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0<br />
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0<br />
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0<br />
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0<br />
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0<br />
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0<br />
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0<br />
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0<br />
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0<br />
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0<br />
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0<br />
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0<br />
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0<br />
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0<br />
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0<br />
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0<br />
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0<br />
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0<br />
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0<br />
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0<br />
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0<br />
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0<br />
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0<br />
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0<br />
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0<br />
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0<br />
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0<br />
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0<br />
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0<br />
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0<br />
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0<br />
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0<br />
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0<br />
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0<br />
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0<br />
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0<br />
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0<br />
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0<br />
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0<br />
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0<br />
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0<br />
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0<br />
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0<br />
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0<br />
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0<br />
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0<br />
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0<br />
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0<br />
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0<br />
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0<br />
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0<br />
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0<br />
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0<br />
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0<br />
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0<br />
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0<br />
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0<br />
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0<br />
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0<br />
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0<br />
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0<br />
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0<br />
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0<br />
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0<br />
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0<br />
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0<br />
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0<br />
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0<br />
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0<br />
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0<br />
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0<br />
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0<br />
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0<br />
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0<br />
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0<br />
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0<br />
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0<br />
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0<br />
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0<br />
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0<br />
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0<br />
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0<br />
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0<br />
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0<br />
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0<br />
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0<br />
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0<br />
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0<br />
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0<br />
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0<br />
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0<br />
CONECT 1 2 0 0 0 NONE 109<br />
CONECT 2 1 3 22 41 NONE 110<br />
CONECT 3 2 4 10 16 NONE 111<br />
CONECT 4 3 9 5 0 NONE 112<br />
CONECT 5 4 6 60 0 NONE 113<br />
CONECT 6 5 7 61 0 NONE 114<br />
CONECT 7 6 8 62 0 NONE 115<br />
CONECT 8 7 9 63 0 NONE 116<br />
CONECT 9 8 4 64 0 NONE 117<br />
CONECT 10 3 15 11 0 NONE 118<br />
CONECT 11 10 12 65 0 NONE 119<br />
CONECT 12 11 13 66 0 NONE 120<br />
CONECT 13 12 14 67 0 NONE 121<br />
CONECT 14 13 15 68 0 NONE 122<br />
CONECT 15 14 10 69 0 NONE 123<br />
CONECT 16 3 21 17 0 NONE 124<br />
CONECT 17 16 18 70 0 NONE 125<br />
CONECT 18 17 19 71 0 NONE 126<br />
CONECT 19 18 20 72 0 NONE 127<br />
CONECT 20 19 21 73 0 NONE 128<br />
CONECT 21 20 16 74 0 NONE 129<br />
CONECT 22 2 23 29 35 NONE 130<br />
CONECT 23 22 28 24 0 NONE 131<br />
CONECT 24 23 25 75 0 NONE 132<br />
CONECT 25 24 26 76 0 NONE 133<br />
CONECT 26 25 27 77 0 NONE 134<br />
CONECT 27 26 28 78 0 NONE 135<br />
CONECT 28 27 23 79 0 NONE 136<br />
CONECT 29 22 34 30 0 NONE 137<br />
CONECT 30 29 31 80 0 NONE 138<br />
CONECT 31 30 32 81 0 NONE 139<br />
CONECT 32 31 33 82 0 NONE 140<br />
CONECT 33 32 34 83 0 NONE 141<br />
CONECT 34 33 29 84 0 NONE 142<br />
CONECT 35 22 40 36 0 NONE 143<br />
CONECT 36 35 37 85 0 NONE 144<br />
CONECT 37 36 38 86 0 NONE 145<br />
CONECT 38 37 39 87 0 NONE 146<br />
CONECT 39 38 40 88 0 NONE 147<br />
CONECT 40 39 35 89 0 NONE 148<br />
CONECT 41 2 42 48 54 NONE 149<br />
CONECT 42 41 47 43 0 NONE 150<br />
CONECT 43 42 44 90 0 NONE 151<br />
CONECT 44 43 45 91 0 NONE 152<br />
CONECT 45 44 46 92 0 NONE 153<br />
CONECT 46 45 47 93 0 NONE 154<br />
CONECT 47 46 42 94 0 NONE 155<br />
CONECT 48 41 53 49 0 NONE 156<br />
CONECT 49 48 50 95 0 NONE 157<br />
CONECT 50 49 51 96 0 NONE 158<br />
CONECT 51 50 52 97 0 NONE 159<br />
CONECT 52 51 53 98 0 NONE 160<br />
CONECT 53 52 48 99 0 NONE 161<br />
CONECT 54 41 59 55 0 NONE 162<br />
CONECT 55 54 56 100 0 NONE 163<br />
CONECT 56 55 57 101 0 NONE 164<br />
CONECT 57 56 58 102 0 NONE 165<br />
CONECT 58 57 59 103 0 NONE 166<br />
CONECT 59 58 54 104 0 NONE 167<br />
END NONE 168</inlineContents><br />
</jmolApplet><br />
</jmol><br />
<br />
==Reaction scheme==<br />
[[Image:Wilkinsons reaction mechanism2.gif]]<br />
[[Image:Example.jpg]]<br />
<br />
==Applications of Wilkinson's Catalyst==<br />
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.<br />
<br />
==References==<br />
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst<br />
# http://www.3dchem.com/molecules.asp?ID=35<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Schwartz.jpg&diff=12846
File:Schwartz.jpg
2007-12-04T15:26:33Z
<p>Sh606: </p>
<hr />
<div></div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=12844
It07:Schwartz
2007-12-04T15:26:19Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is an air, moisture, and moderately light sensitive compound. Therefore, it should be stored in the dark, dry place.<br />
<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation]]<br />
<br />
==IR spectrum==<br />
[[Image:schwartz.jpg|thumb|center|1000|schwartz]]<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=12843
It07:Schwartz
2007-12-04T15:24:04Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is an air, moisture, and moderately light sensitive compound. Therefore, it should be stored in the dark, dry place.<br />
<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:sch.jpg|thumb|center|1000|Hydrozirconation]]<br />
<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Hydrozirconation_1.gif&diff=12842
File:Hydrozirconation 1.gif
2007-12-04T15:23:20Z
<p>Sh606: </p>
<hr />
<div></div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=It07:Schwartz&diff=12841
It07:Schwartz
2007-12-04T15:23:03Z
<p>Sh606: </p>
<hr />
<div><noinclude><br />
<!-- This template has been defined after elaborate discussion in the Chemicals Wikiproject. Please do not add, deleted or otherwise change it unless after due discussion in [[wikipedia talk:WikiProject Chemicals]] --><br />
</noinclude>{| class="toccolours" border="1" style="float: right; clear: right; margin: 0 0 1em 1em; border-collapse: collapse; width: 280px"<br />
! {{chembox header}} | {{PAGENAME}} <!-- replace if not identical with the article name --><br />
|-<br />
| align="center" colspan="2" bgcolor="#ffffff" |[[Image:Schwartz's_Reagent.png|thumb|center|200|Schwartz's_Reagent]] <br />
|-<br />
! {{chembox header}} | General<br />
|- <br />
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]<br />
| Bis(η5-cyclopentadienyl)- zirconium(IV) chloride hydride<br />
<br />
|-<br />
| Other names<br />
| Cp2ZrClH, zirconocene chloride hydride<br />
|-<br />
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]<br />
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh C<sub>10</sub>H<sub>11</sub>ClZr<br />
|-<br />
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]<br />
| 257.87 g/mol<sup>-1</sup><br />
|-<br />
! {{chembox header}} | Identifier<br />
|-<br />
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]<br />
| 37342-97-5<br />
|-<br />
! {{chembox header}} | Properties<br />
|-<br />
| Appearance<br />
| White Solid<br />
|-<br />
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25&nbsp;°C, 100&nbsp;kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small><br />
|-<br />
|}<br />
<br />
==Schwartz reagent==<br />
Schwartz's reagent is the commonly used name for the chemical compound with the formula (C<sub>5</sub>H<sub>5</sub>)<sub>2</sub>ZrHCl. This metallocene is used in organic synthesis for many transformations of alkenes and alkynes. Schwartz's Reagent is an air, moisture, and moderately light sensitive compound. Therefore, it should be stored in the dark, dry place.<br />
<br />
<br />
== 3D Model of Schwartz reagent ==<br />
<br />
<br />
<jmol><br />
<jmolApplet><br />
<size>400</size><br />
<title>Sibutramine</title><color>white</color><br />
<uploadedFileContents>schwartz reagent.pdb</uploadedFileContents><br />
</jmolApplet><br />
<br />
<jmolMenu><br />
<item><text>Start spinning</text><script>spin on</script></item><br />
<item><text>Stop spinning</text><script>spin off</script></item><br />
<menuHeight>-1</menuHeight><br />
</jmolMenu><br />
<br />
<br />
</jmol><br />
<br />
<br><br />
<br />
==Uses==<br />
Schwartz's reagent is used as a reagent for the functionalization of olefins and alkynes and it is also used in conversion of amides to aldehydes. <br />
<br />
<br />
==Hydrozirconation reaction==<br />
Schwartz's reagent reacts with alkenes and alkynes via called hydrozirconation. This reaction results in the addition of the Zr-H bond across the C=C or C≡C bond. In this reaction the insertion of either a terminal or internal olefin gives the same product. The order of the olefin reactivity is terminal alkyne > terminal alkene ~ internal alkyne > disubstituted alkene. This isomerization occurs through a series of beta-hydride elimination and olefin insertion reactions as shown below. [[Image:hydrozirconation_1.gif|thumb|center|1000|Hydrozirconation]]<br />
<br />
<br />
==Reference==<br />
# http://en.wikipedia.org/wiki/Schwartz's_reagent<br />
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/223670<br />
# http://www.ilpi.com/organomet/hydzirc.html</div>
Sh606
https://chemwiki.ch.ic.ac.uk/index.php?title=File:Hydrozirconation_1.jpg&diff=12839
File:Hydrozirconation 1.jpg
2007-12-04T15:21:32Z
<p>Sh606: </p>
<hr />
<div></div>
Sh606