ChemWiki - User contributions [en]

File:Infra-red.jpg

2007-11-29T17:07:31Z

Shy06:

2007-11-29T17:04:07Z

Shy06:

It07:wilkinson

2007-11-29T17:00:33Z

Shy06:

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104112 0 0 0 1 V2000
0.4884 -0.1610 -0.1106 Rh 0 0 0 0 0
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0.2381 4.0214 -4.7685 C 0 0 0 0 0
0.8850 4.3392 -3.5753 C 0 0 0 0 0
1.3168 3.3241 -2.7189 C 0 0 0 0 0
3.2256 1.6612 -1.1825 C 0 0 0 0 0
4.2895 2.0906 -1.9837 C 0 0 0 0 0
5.3078 2.8854 -1.4532 C 0 0 0 0 0
5.2415 3.3147 -0.1271 C 0 0 0 0 0
4.1415 2.9626 0.6556 C 0 0 0 0 0
3.1433 2.1422 0.1273 C 0 0 0 0 0
2.5553 -0.6693 -2.9837 C 0 0 0 0 0
1.7496 -1.4378 -3.8325 C 0 0 0 0 0
2.2861 -2.4006 -4.6897 C 0 0 0 0 0
3.6580 -2.6491 -4.6887 C 0 0 0 0 0
4.4770 -1.9229 -3.8252 C 0 0 0 0 0
3.9271 -0.9472 -2.9908 C 0 0 0 0 0
1.8066 0.6402 -1.8755 P 0 3 0 0 0
2.4895 -3.0116 -0.7006 C 0 0 0 0 0
1.4692 -3.3726 -1.5868 C 0 0 0 0 0
1.6312 -4.4478 -2.4627 C 0 0 0 0 0
2.8163 -5.1844 -2.4521 C 0 0 0 0 0
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0.2341 -4.5961 2.7283 C 0 0 0 0 0
0.6105 -3.6936 1.7315 C 0 0 0 0 0
3.7082 -0.8006 1.1206 C 0 0 0 0 0
4.9447 -0.9029 0.4774 C 0 0 0 0 0
6.0713 -0.2464 0.9766 C 0 0 0 0 0
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3.6218 -0.0078 2.2721 C 0 0 0 0 0
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-1.2673 1.3055 -0.7138 P 0 3 0 0 0
-1.9600 0.9997 -2.4063 C 0 0 0 0 0
-2.8510 1.8725 -3.0379 C 0 0 0 0 0
-3.3692 1.5738 -4.2997 C 0 0 0 0 0
-3.0491 0.3654 -4.9203 C 0 0 0 0 0
-2.2384 -0.5554 -4.2555 C 0 0 0 0 0
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-0.7810 3.0491 -0.3062 C 0 0 0 0 0
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2.2746 1.8922 0.7534 H 0 0 0 0 0
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-0.8555 6.3149 -1.3365 H 0 0 0 0 0
-1.5785 4.0746 -2.0551 H 0 0 0 0 0
-3.1824 -0.9476 -0.6037 H 0 0 0 0 0
-5.2797 -1.3605 0.6443 H 0 0 0 0 0
-6.1750 0.3688 2.2115 H 0 0 0 0 0
-4.9429 2.5200 2.5189 H 0 0 0 0 0
-2.8474 2.9476 1.2892 H 0 0 0 0 0
1 20 1 6 0 0
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1 41 1 0 0 0
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59104 1 0 0 0
M END
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|-

|-
! {{chembox header}} | General
|-
| [http://en.wikipedia.org/wiki/IUPAC Systematic name]
| chlorotris(triphenylphosphine)rhodium(I)

|-
| Other names
| Rhodium(I) tris-
(triphenylphosphine) chloride,
Wilkinson’s catalyst,
Tris(triphenylphosphine)-
rhodium chloride
|-
| [http://en.wikipedia.org/wiki/Chemical_formula Molecular formula]
| C<sub>54</sub>H<sub>45</sub>ClP<sub>3</sub>Rh
|-
| [http://en.wikipedia.org/wiki/Molar_mass Molar mass]
| 925.22 g/mol<sup>-1</sup>
|-
| [http://en.wikipedia.org/wiki/CAS_registry_number CAS number]
| 14694-95-2
|-
! {{chembox header}} | Properties
|-
| [http://en.wikipedia.org/wiki/Melting_point Melting point]
| 245-250 °C
|-
|Appearance
|Red Crystalline Solid
|-
! {{chembox header}} | spectrum
|-
| 13C NMR
| [[Image:NMR.jpg]]
|-
| 1H NMR
|[[Image:NMR.jpg]]
|-
| IR
|[[Image:IR.jpg]]
|-
| MS
|[http://www.chemexper.com/cheminfo/servlet/org.chemcalc.ChemCalc?isograph=on&mformula=C54H45ClP3Rh]

|-
| {{chembox header}} | <small>Except where noted otherwise, data are given for<br /> materials in their [[standard state|standard state (at 25 °C, 100 kPa)]]<br />[[wikipedia:Chemical infobox|Infobox disclaimer and references]]</small>
|-
|}

== Wilkinson's Catalyst ==

Wilkinson's catalyst is the common name for chlorotris(triphenylphosphine)rhodium(I).
It is a chemical compound with the formula RhCl(PPh3)3, where Ph represents phenyl group. It is named after the late organometallic chemist and 1973 Nobel Laureate, Sir Geoffrey Wilkinson who popularlized its use.

==History of Geoffrey Wilkinson==
[[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.

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).

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.

His work had a wide effect on inorganic chemistry and started the field of organometallic chemistry.
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.

Wilkinson's Catalyst is a rhodium metal complex with three large phosphine ligands coordinated to the metal centre, Rh(PPh3)3Cl.

==Synthesis==
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.
RhCl3(H2O)3 + CH3CH2OH + 3 PPh3 → RhCl(PPh3)3 + CH3CHO + 2 HCl + 3 H2O

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<inlineContents>HEADER NONAME 19-Nov-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 19-Nov-07 0 NONE 4
ATOM 1 Cl 0 0.481 0.749 -2.633 0.00 0.00 Cl+0
ATOM 2 Rh 0 0.361 0.240 -0.527 0.00 0.00 Rh+0
ATOM 3 P 0 2.453 0.144 0.350 0.00 0.00 P+0
ATOM 4 C 0 4.176 0.066 1.071 0.00 0.00 C+0
ATOM 5 C 0 4.364 0.233 2.431 0.00 0.00 C+0
ATOM 6 C 0 5.638 0.175 2.964 0.00 0.00 C+0
ATOM 7 C 0 6.724 -0.051 2.138 0.00 0.00 C+0
ATOM 8 C 0 6.535 -0.219 0.779 0.00 0.00 C+0
ATOM 9 C 0 5.261 -0.166 0.246 0.00 0.00 C+0
ATOM 10 C 0 3.149 -0.206 -1.350 0.00 0.00 C+0
ATOM 11 C 0 4.183 -1.112 -1.501 0.00 0.00 C+0
ATOM 12 C 0 4.697 -1.371 -2.757 0.00 0.00 C+0
ATOM 13 C 0 4.177 -0.725 -3.863 0.00 0.00 C+0
ATOM 14 C 0 3.143 0.179 -3.713 0.00 0.00 C+0
ATOM 15 C 0 2.625 0.435 -2.457 0.00 0.00 C+0
ATOM 16 C 0 1.925 -1.269 1.454 0.00 0.00 C+0
ATOM 17 C 0 2.285 -1.275 2.789 0.00 0.00 C+0
ATOM 18 C 0 1.895 -2.320 3.606 0.00 0.00 C+0
ATOM 19 C 0 1.146 -3.360 3.087 0.00 0.00 C+0
ATOM 20 C 0 0.786 -3.354 1.753 0.00 0.00 C+0
ATOM 21 C 0 1.172 -2.307 0.937 0.00 0.00 C+0
ATOM 22 P 0 -0.846 1.822 0.567 0.00 0.00 P+0
ATOM 23 C 0 -1.840 3.125 1.467 0.00 0.00 C+0
ATOM 24 C 0 -2.544 2.791 2.609 0.00 0.00 C+0
ATOM 25 C 0 -3.279 3.754 3.274 0.00 0.00 C+0
ATOM 26 C 0 -3.309 5.052 2.798 0.00 0.00 C+0
ATOM 27 C 0 -2.604 5.386 1.657 0.00 0.00 C+0
ATOM 28 C 0 -1.866 4.424 0.994 0.00 0.00 C+0
ATOM 29 C 0 0.053 3.161 -0.380 0.00 0.00 C+0
ATOM 30 C 0 -0.043 4.479 0.028 0.00 0.00 C+0
ATOM 31 C 0 0.621 5.469 -0.672 0.00 0.00 C+0
ATOM 32 C 0 1.381 5.141 -1.779 0.00 0.00 C+0
ATOM 33 C 0 1.478 3.824 -2.186 0.00 0.00 C+0
ATOM 34 C 0 0.817 2.833 -1.484 0.00 0.00 C+0
ATOM 35 C 0 -2.425 1.091 -0.119 0.00 0.00 C+0
ATOM 36 C 0 -3.609 1.800 -0.033 0.00 0.00 C+0
ATOM 37 C 0 -4.776 1.260 -0.540 0.00 0.00 C+0
ATOM 38 C 0 -4.759 0.011 -1.133 0.00 0.00 C+0
ATOM 39 C 0 -3.575 -0.697 -1.220 0.00 0.00 C+0
ATOM 40 C 0 -2.407 -0.155 -0.717 0.00 0.00 C+0
ATOM 41 P 0 -0.651 -1.779 -0.293 0.00 0.00 P+0
ATOM 42 C 0 -1.484 -3.442 -0.100 0.00 0.00 C+0
ATOM 43 C 0 -1.162 -4.479 -0.956 0.00 0.00 C+0
ATOM 44 C 0 -1.778 -5.708 -0.813 0.00 0.00 C+0
ATOM 45 C 0 -2.715 -5.901 0.185 0.00 0.00 C+0
ATOM 46 C 0 -3.035 -4.864 1.041 0.00 0.00 C+0
ATOM 47 C 0 -2.416 -3.636 0.902 0.00 0.00 C+0
ATOM 48 C 0 -1.168 -1.319 1.445 0.00 0.00 C+0
ATOM 49 C 0 -1.730 -2.271 2.274 0.00 0.00 C+0
ATOM 50 C 0 -2.112 -1.931 3.558 0.00 0.00 C+0
ATOM 51 C 0 -1.932 -0.638 4.013 0.00 0.00 C+0
ATOM 52 C 0 -1.369 0.314 3.184 0.00 0.00 C+0
ATOM 53 C 0 -0.983 -0.027 1.901 0.00 0.00 C+0
ATOM 54 C 0 -1.771 -1.385 -1.737 0.00 0.00 C+0
ATOM 55 C 0 -2.565 -2.374 -2.285 0.00 0.00 C+0
ATOM 56 C 0 -3.394 -2.083 -3.353 0.00 0.00 C+0
ATOM 57 C 0 -3.428 -0.803 -3.872 0.00 0.00 C+0
ATOM 58 C 0 -2.634 0.187 -3.323 0.00 0.00 C+0
ATOM 59 C 0 -1.809 -0.103 -2.253 0.00 0.00 C+0
ATOM 60 H 0 3.516 0.410 3.076 0.00 0.00 H+0
ATOM 61 H 0 5.786 0.306 4.026 0.00 0.00 H+0
ATOM 62 H 0 7.719 -0.096 2.555 0.00 0.00 H+0
ATOM 63 H 0 7.383 -0.396 0.134 0.00 0.00 H+0
ATOM 64 H 0 5.114 -0.297 -0.815 0.00 0.00 H+0
ATOM 65 H 0 4.589 -1.616 -0.636 0.00 0.00 H+0
ATOM 66 H 0 5.505 -2.077 -2.874 0.00 0.00 H+0
ATOM 67 H 0 4.580 -0.927 -4.845 0.00 0.00 H+0
ATOM 68 H 0 2.737 0.683 -4.578 0.00 0.00 H+0
ATOM 69 H 0 1.817 1.142 -2.340 0.00 0.00 H+0
ATOM 70 H 0 2.870 -0.462 3.194 0.00 0.00 H+0
ATOM 71 H 0 2.176 -2.324 4.648 0.00 0.00 H+0
ATOM 72 H 0 0.842 -4.176 3.725 0.00 0.00 H+0
ATOM 73 H 0 0.201 -4.166 1.348 0.00 0.00 H+0
ATOM 74 H 0 0.891 -2.302 -0.106 0.00 0.00 H+0
ATOM 75 H 0 -2.521 1.777 2.980 0.00 0.00 H+0
ATOM 76 H 0 -3.830 3.493 4.166 0.00 0.00 H+0
ATOM 77 H 0 -3.884 5.804 3.318 0.00 0.00 H+0
ATOM 78 H 0 -2.628 6.400 1.286 0.00 0.00 H+0
ATOM 79 H 0 -1.315 4.685 0.103 0.00 0.00 H+0
ATOM 80 H 0 -0.637 4.734 0.893 0.00 0.00 H+0
ATOM 81 H 0 0.545 6.498 -0.354 0.00 0.00 H+0
ATOM 82 H 0 1.900 5.915 -2.326 0.00 0.00 H+0
ATOM 83 H 0 2.072 3.568 -3.051 0.00 0.00 H+0
ATOM 84 H 0 0.893 1.804 -1.802 0.00 0.00 H+0
ATOM 85 H 0 -3.622 2.775 0.431 0.00 0.00 H+0
ATOM 86 H 0 -5.701 1.813 -0.472 0.00 0.00 H+0
ATOM 87 H 0 -5.671 -0.411 -1.528 0.00 0.00 H+0
ATOM 88 H 0 -3.562 -1.672 -1.683 0.00 0.00 H+0
ATOM 89 H 0 -1.482 -0.708 -0.785 0.00 0.00 H+0
ATOM 90 H 0 -0.431 -4.329 -1.736 0.00 0.00 H+0
ATOM 91 H 0 -1.528 -6.519 -1.482 0.00 0.00 H+0
ATOM 92 H 0 -3.197 -6.861 0.296 0.00 0.00 H+0
ATOM 93 H 0 -3.767 -5.014 1.821 0.00 0.00 H+0
ATOM 94 H 0 -2.667 -2.826 1.571 0.00 0.00 H+0
ATOM 95 H 0 -1.871 -3.281 1.918 0.00 0.00 H+0
ATOM 96 H 0 -2.552 -2.675 4.205 0.00 0.00 H+0
ATOM 97 H 0 -2.231 -0.372 5.016 0.00 0.00 H+0
ATOM 98 H 0 -1.228 1.324 3.540 0.00 0.00 H+0
ATOM 99 H 0 -0.543 0.717 1.254 0.00 0.00 H+0
ATOM 100 H 0 -2.539 -3.375 -1.880 0.00 0.00 H+0
ATOM 101 H 0 -4.014 -2.856 -3.782 0.00 0.00 H+0
ATOM 102 H 0 -4.074 -0.575 -4.707 0.00 0.00 H+0
ATOM 103 H 0 -2.660 1.188 -3.729 0.00 0.00 H+0
ATOM 104 H 0 -1.189 0.670 -1.824 0.00 0.00 H+0
CONECT 1 2 0 0 0 NONE 109
CONECT 2 1 3 22 41 NONE 110
CONECT 3 2 4 10 16 NONE 111
CONECT 4 3 9 5 0 NONE 112
CONECT 5 4 6 60 0 NONE 113
CONECT 6 5 7 61 0 NONE 114
CONECT 7 6 8 62 0 NONE 115
CONECT 8 7 9 63 0 NONE 116
CONECT 9 8 4 64 0 NONE 117
CONECT 10 3 15 11 0 NONE 118
CONECT 11 10 12 65 0 NONE 119
CONECT 12 11 13 66 0 NONE 120
CONECT 13 12 14 67 0 NONE 121
CONECT 14 13 15 68 0 NONE 122
CONECT 15 14 10 69 0 NONE 123
CONECT 16 3 21 17 0 NONE 124
CONECT 17 16 18 70 0 NONE 125
CONECT 18 17 19 71 0 NONE 126
CONECT 19 18 20 72 0 NONE 127
CONECT 20 19 21 73 0 NONE 128
CONECT 21 20 16 74 0 NONE 129
CONECT 22 2 23 29 35 NONE 130
CONECT 23 22 28 24 0 NONE 131
CONECT 24 23 25 75 0 NONE 132
CONECT 25 24 26 76 0 NONE 133
CONECT 26 25 27 77 0 NONE 134
CONECT 27 26 28 78 0 NONE 135
CONECT 28 27 23 79 0 NONE 136
CONECT 29 22 34 30 0 NONE 137
CONECT 30 29 31 80 0 NONE 138
CONECT 31 30 32 81 0 NONE 139
CONECT 32 31 33 82 0 NONE 140
CONECT 33 32 34 83 0 NONE 141
CONECT 34 33 29 84 0 NONE 142
CONECT 35 22 40 36 0 NONE 143
CONECT 36 35 37 85 0 NONE 144
CONECT 37 36 38 86 0 NONE 145
CONECT 38 37 39 87 0 NONE 146
CONECT 39 38 40 88 0 NONE 147
CONECT 40 39 35 89 0 NONE 148
CONECT 41 2 42 48 54 NONE 149
CONECT 42 41 47 43 0 NONE 150
CONECT 43 42 44 90 0 NONE 151
CONECT 44 43 45 91 0 NONE 152
CONECT 45 44 46 92 0 NONE 153
CONECT 46 45 47 93 0 NONE 154
CONECT 47 46 42 94 0 NONE 155
CONECT 48 41 53 49 0 NONE 156
CONECT 49 48 50 95 0 NONE 157
CONECT 50 49 51 96 0 NONE 158
CONECT 51 50 52 97 0 NONE 159
CONECT 52 51 53 98 0 NONE 160
CONECT 53 52 48 99 0 NONE 161
CONECT 54 41 59 55 0 NONE 162
CONECT 55 54 56 100 0 NONE 163
CONECT 56 55 57 101 0 NONE 164
CONECT 57 56 58 102 0 NONE 165
CONECT 58 57 59 103 0 NONE 166
CONECT 59 58 54 104 0 NONE 167
END NONE 168</inlineContents>
</jmolApplet>
</jmol>

==Reaction scheme==
[[Image:Wilkinsons reaction mechanism2.gif]]
[[Image:Example.jpg]]

==Applications of Wilkinson's Catalyst==
One of the major uses of wilkinson's catalyst is it's use in the hydrogentation of alkenes.

==References==
# http://en.wikipedia.org/wiki/Wilkinson%27s_catalyst
# http://www.3dchem.com/molecules.asp?ID=35
# http://www.sigmaaldrich.com/catalog/search/ProductDetail/ALDRICH/205036

File:1H NMR.jpg

2007-11-28T22:43:28Z

Shy06:

File:1HNMR.jpg

2007-11-28T22:40:21Z

Shy06:

2007-11-13T15:54:05Z

Shy06: /* Uses and side effects */

=Introduction=
{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem = 24895349
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
melting_point= 177-182C (deg)

| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Cation = May be irritating to gastrointestinal tract. Large does have caused edema of lungs, | shortness of breath and paralysis in animals. Toxic to nonruminant animals, such as humans, | | by reducing the capacity the blood has to carry oxygen.
| Legal_status =
| Routes =
}}

{| border="1" cellspacing="0" colspan="2" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy UV-Vis]
|-
| [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy λ<sub>max</sub>]
| ? [http://en.wikipedia.org/wiki/Nanometre nm]
|-
| [http://en.wikipedia.org/wiki/Extinction_coefficient Extinction coefficient], ε
| ?
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Infrared_spectroscopy IR]
|-
| Major absorption bands
| ? [http://en.wikipedia.org/wiki/Centimetre cm]<sup>−1</sup>
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/NMR_Spectroscopy NMR]
|-
| [http://en.wikipedia.org/wiki/Proton_NMR Proton NMR] 
|  
|-
| [http://en.wikipedia.org/wiki/Carbon-13_NMR Carbon-13 NMR] 
| [https://www.ch.imperial.ac.uk/wiki/images/b/bd/Gossypol_C13NMR.jpg Carbon-13NMR]
|-
| Other NMR data 
|  
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Mass_Spectrometry MS]
|-
| Masses of <br>main fragments
|   
|-
|}

Gossypol, C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>, is a pigment named after the species of cotton ''gossypium L., malvaceae'', that bears the seeds from which it is extracted. Initially known only as an undesirable toxin found in foods that contained cottonseed oil, it was thought to have potential uses as a rubber antioxidant, a stabilizer for vinyl polymers and as a potential insecticide. Today it is known primarily as a male oral contraceptive, after the discovery of remarkable fertility suppressive effects in men.

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
</jmolApplet>
</jmol>

= History =

In 1929, to investigate anecdotal evidence that families who cooked with crude cottonseed oil produced fewer children, a large scale Chinese fertility survey was carried out. The study concluded that it was this oil that affected male fertility, and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception. '[I'd like to see sources for the previous paragraph please]'

In late 2005, a team of researchers at Sunderland University found that gossypol has been seen to help stop the spread of psoriasis, a fairly common and unpleasant genetic skin condition, as well as reducing inflammation in sufferers. Psoriasis suffers have a genetic fault that means that under certain conditions their skin starts to produce far too many skin cells.

=Uses and side effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organisation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.<ref>http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=9639146&dopt=Citation</ref>

Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis<ref>http://www.clevelandclinic.org/health/health-info/docs/2400/2452.asp?index=9499</ref> is also known as 'familial paralysis', and occurs due to low levels of potassium in the body. During an attack of paralysis, muscle weakness occurs in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal. Also there are few other toxic symptoms such as reptosprisis, heart failure and jaundice.

Recovery of those who used gossypol is 75%; however, it can lead to other related symptoms such as smaller testicular colume, and elevated follicle stimulating hormone concentrations.

= Known hazards =

May be irritating to gastrointestinal tract. Large doses have caused edema of lungs, shortness of breath and paralysis in animals. Toxic to nonruminant animals such as humans, by reducing the capacity the blood has to carry oxygen.

A large-scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects.

A man who uses the drug for protracted periods could become partially, if not fully, infertile.

= References =
<references/>

*http://www.emolecules.com/cgi-bin/more?vid=538892#

*The Merck Index- An Encylopedia of Chemicals, Drugs and Biologicals, Thirteenth edition, Merck & Co., Inc.

*http://news.bbc.co.uk/1/hi/england/wear/4284602.stm

*http://www.malecontraceptives.org/methods/gossypol.php

It07:Gossypol

2007-11-13T15:23:15Z

Shy06: /* Introduction */

=Introduction=
{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem = 24895349
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
melting_point= 177-182C (deg)

| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Cation = May be irritating to gastrointestinal tract. Large does have caused edema of lungs, | shortness of breath and paralysis in animals. Toxic to nonruminant animals, such as humans, | | by reducing the capacity the blood has to carry oxygen.
| Legal_status =
| Routes =
}}

{| border="1" cellspacing="0" colspan="2" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy UV-Vis]
|-
| [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy λ<sub>max</sub>]
| ? [http://en.wikipedia.org/wiki/Nanometre nm]
|-
| [http://en.wikipedia.org/wiki/Extinction_coefficient Extinction coefficient], ε
| ?
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Infrared_spectroscopy IR]
|-
| Major absorption bands
| ? [http://en.wikipedia.org/wiki/Centimetre cm]<sup>−1</sup>
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/NMR_Spectroscopy NMR]
|-
| [http://en.wikipedia.org/wiki/Proton_NMR Proton NMR] 
|  
|-
| [http://en.wikipedia.org/wiki/Carbon-13_NMR Carbon-13 NMR] 
| [https://www.ch.imperial.ac.uk/wiki/images/b/bd/Gossypol_C13NMR.jpg Carbon-13NMR]
|-
| Other NMR data 
|  
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Mass_Spectrometry MS]
|-
| Masses of <br>main fragments
|   
|-
|}

Gossypol, C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>, is a pigment named after the species of cotton ''gossypium L., malvaceae'', that bears the seeds from which it is extracted. Initially known only as an undesirable toxin found in foods that contained cottonseed oil, it was thought to have potential uses as a rubber antioxidant, a stabilizer for vinyl polymers and as a potential insecticide. Today it is known primarily as a male oral contraceptive, after the discovery of remarkable fertility suppressive effects in men.

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
</jmolApplet>
</jmol>

= History =

In 1929, to investigate anecdotal evidence that families who cooked with crude cottonseed oil produced fewer children, a large scale Chinese fertility survey was carried out. The study concluded that it was this oil that affected male fertility, and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception. '[I'd like to see sources for the previous paragraph please]'

In late 2005, a team of researchers at Sunderland University found that gossypol has been seen to help stop the spread of psoriasis, a fairly common and unpleasant genetic skin condition, as well as reducing inflammation in sufferers. Psoriasis suffers have a genetic fault that means that under certain conditions their skin starts to produce far too many skin cells.

=Uses and side effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organisation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.<ref>http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=9639146&dopt=Citation</ref>

Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis<ref>http://www.clevelandclinic.org/health/health-info/docs/2400/2452.asp?index=9499</ref> is also known as 'familial paralysis', and occurs due to low levels of potassium in the body. During an attack of paralysis, muscle weakness occurs in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal.

Recovery of those who used gossypol is 75%; however, it can lead to other related symptoms such as smaller testicular colume, and elevated follicle stimulating hormone concentrations.

= Known hazards =

May be irritating to gastrointestinal tract. Large doses have caused edema of lungs, shortness of breath and paralysis in animals. Toxic to nonruminant animals such as humans, by reducing the capacity the blood has to carry oxygen.

A large-scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects.

A man who uses the drug for protracted periods could become partially, if not fully, infertile.

= References =
<references/>

*http://www.emolecules.com/cgi-bin/more?vid=538892#

*The Merck Index- An Encylopedia of Chemicals, Drugs and Biologicals, Thirteenth edition, Merck & Co., Inc.

*http://news.bbc.co.uk/1/hi/england/wear/4284602.stm

*http://www.malecontraceptives.org/methods/gossypol.php

It07:Gossypol

2007-11-13T15:21:08Z

Shy06: /* Introduction */

=Introduction=
{{Drug-Box |
| Box_Name = Gossypol
| ImageFile = Maingossypol.png
| IUPACName = 2,2′-bis-(Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene)
| OtherName = Gossypol
| CAS_No = 303-45-7
| ATC_Code =
| PubChem = 24895349
| SMILES = CC(C)C1=C(C=C(C)C(C3=C(O)C(C(C=O)=C(O)C(O)=C4C(C)C)=C4C=C3C)=C2O)C2=C(C=O)C(O)=C1O
| Formula = C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>
| MolarMass = 518.554
| Bioavailability =
| Protein_binding
melting point= 177-182C (deg)

| Metabolism =
| Half_life =
| Excretion =
| Pregnancy_cat =
| Cation = May be irritating to gastrointestinal tract. Large does have caused edema of lungs, | shortness of breath and paralysis in animals. Toxic to nonruminant animals, such as humans, | | by reducing the capacity the blood has to carry oxygen.
| Legal_status =
| Routes =
}}

{| border="1" cellspacing="0" colspan="2" cellpadding="3" style="margin: 0 0 0 0.5em; background: #FFFFFF; border-collapse: collapse; border-color: #C0C090;"
! {{chembox header}} | [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy UV-Vis]
|-
| [http://en.wikipedia.org/wiki/UV/VIS_spectroscopy λ<sub>max</sub>]
| ? [http://en.wikipedia.org/wiki/Nanometre nm]
|-
| [http://en.wikipedia.org/wiki/Extinction_coefficient Extinction coefficient], ε
| ?
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Infrared_spectroscopy IR]
|-
| Major absorption bands
| ? [http://en.wikipedia.org/wiki/Centimetre cm]<sup>−1</sup>
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/NMR_Spectroscopy NMR]
|-
| [http://en.wikipedia.org/wiki/Proton_NMR Proton NMR] 
|  
|-
| [http://en.wikipedia.org/wiki/Carbon-13_NMR Carbon-13 NMR] 
| [https://www.ch.imperial.ac.uk/wiki/images/b/bd/Gossypol_C13NMR.jpg Carbon-13NMR]
|-
| Other NMR data 
|  
|-
! {{chembox header}} | [http://en.wikipedia.org/wiki/Mass_Spectrometry MS]
|-
| Masses of <br>main fragments
|   
|-
|}

Gossypol, C<sub>30</sub>H<sub>30</sub>O<sub>8</sub>, is a pigment named after the species of cotton ''gossypium L., malvaceae'', that bears the seeds from which it is extracted. Initially known only as an undesirable toxin found in foods that contained cottonseed oil, it was thought to have potential uses as a rubber antioxidant, a stabilizer for vinyl polymers and as a potential insecticide. Today it is known primarily as a male oral contraceptive, after the discovery of remarkable fertility suppressive effects in men.

<jmol>
<jmolApplet>
<size>400</size>
<color>black</color>
<script>zoom 80;frame 1; move 675 0 10 0 0 0 0 0 3; delay 1;</script>
<inlineContents>gossypol.PDB
HEADER NONAME 18-Oct-07 NONE 1
TITLE NONE 2
AUTHOR WWW daemon apache NONE 3
REVDAT 1 18-Oct-07 0 NONE 4
ATOM 1 C 0 6.511 0.977 2.467 0.00 0.00 C+0
ATOM 2 C 0 5.499 1.668 1.551 0.00 0.00 C+0
ATOM 3 C 0 6.209 2.748 0.731 0.00 0.00 C+0
ATOM 4 C 0 4.888 0.652 0.621 0.00 0.00 C+0
ATOM 5 C 0 3.493 0.469 0.614 0.00 0.00 C+0
ATOM 6 C 0 2.662 1.221 1.464 0.00 0.00 C+0
ATOM 7 C 0 1.316 1.031 1.444 0.00 0.00 C+0
ATOM 8 C 0 0.437 1.843 2.359 0.00 0.00 C+0
ATOM 9 C 0 0.734 0.088 0.583 0.00 0.00 C+0
ATOM 10 C 0 -0.735 -0.099 0.581 0.00 0.00 C+0
ATOM 11 C 0 -1.528 0.659 -0.275 0.00 0.00 C+0
ATOM 12 O 0 -0.962 1.571 -1.107 0.00 0.00 O+0
ATOM 13 C 0 -1.318 -1.045 1.436 0.00 0.00 C+0
ATOM 14 C 0 -0.441 -1.861 2.351 0.00 0.00 C+0
ATOM 15 C 0 -2.664 -1.235 1.453 0.00 0.00 C+0
ATOM 16 C 0 -3.494 -0.480 0.604 0.00 0.00 C+0
ATOM 17 C 0 -2.916 0.474 -0.268 0.00 0.00 C+0
ATOM 18 C 0 -3.791 1.255 -1.147 0.00 0.00 C+0
ATOM 19 C 0 -3.235 2.248 -2.063 0.00 0.00 C+0
ATOM 20 O 0 -3.976 2.955 -2.715 0.00 0.00 O+0
ATOM 21 C 0 -5.170 1.028 -1.091 0.00 0.00 C+0
ATOM 22 O 0 -6.004 1.735 -1.892 0.00 0.00 O+0
ATOM 23 C 0 -5.692 0.073 -0.211 0.00 0.00 C+0
ATOM 24 O 0 -7.036 -0.130 -0.175 0.00 0.00 O+0
ATOM 25 C 0 -4.888 -0.662 0.607 0.00 0.00 C+0
ATOM 26 C 0 -5.503 -1.678 1.536 0.00 0.00 C+0
ATOM 27 C 0 -6.516 -0.986 2.450 0.00 0.00 C+0
ATOM 28 C 0 -6.211 -2.757 0.714 0.00 0.00 C+0
ATOM 29 C 0 1.531 -0.671 -0.270 0.00 0.00 C+0
ATOM 30 O 0 0.967 -1.583 -1.104 0.00 0.00 O+0
ATOM 31 C 0 2.919 -0.485 -0.259 0.00 0.00 C+0
ATOM 32 C 0 3.796 -1.262 -1.140 0.00 0.00 C+0
ATOM 33 C 0 3.242 -2.255 -2.058 0.00 0.00 C+0
ATOM 34 O 0 3.968 -2.822 -2.849 0.00 0.00 O+0
ATOM 35 C 0 5.173 -1.031 -1.084 0.00 0.00 C+0
ATOM 36 O 0 6.009 -1.734 -1.887 0.00 0.00 O+0
ATOM 37 C 0 5.693 -0.072 -0.206 0.00 0.00 C+0
ATOM 38 O 0 7.036 0.134 -0.170 0.00 0.00 O+0
ATOM 39 H 0 6.953 1.712 3.140 0.00 0.00 H+0
ATOM 40 H 0 6.006 0.208 3.051 0.00 0.00 H+0
ATOM 41 H 0 7.294 0.519 1.864 0.00 0.00 H+0
ATOM 42 H 0 4.716 2.126 2.154 0.00 0.00 H+0
ATOM 43 H 0 6.992 2.290 0.127 0.00 0.00 H+0
ATOM 44 H 0 5.488 3.240 0.078 0.00 0.00 H+0
ATOM 45 H 0 6.651 3.483 1.403 0.00 0.00 H+0
ATOM 46 H 0 3.093 1.950 2.133 0.00 0.00 H+0
ATOM 47 H 0 0.134 2.760 1.852 0.00 0.00 H+0
ATOM 48 H 0 -0.448 1.264 2.622 0.00 0.00 H+0
ATOM 49 H 0 0.989 2.095 3.265 0.00 0.00 H+0
ATOM 50 H 0 -0.762 1.109 -1.933 0.00 0.00 H+0
ATOM 51 H 0 -0.323 -1.341 3.301 0.00 0.00 H+0
ATOM 52 H 0 -0.903 -2.834 2.524 0.00 0.00 H+0
ATOM 53 H 0 0.536 -2.001 1.888 0.00 0.00 H+0
ATOM 54 H 0 -3.097 -1.968 2.118 0.00 0.00 H+0
ATOM 55 H 0 -2.164 2.354 -2.159 0.00 0.00 H+0
ATOM 56 H 0 -6.096 1.232 -2.713 0.00 0.00 H+0
ATOM 57 H 0 -7.232 -0.820 -0.824 0.00 0.00 H+0
ATOM 58 H 0 -4.721 -2.136 2.141 0.00 0.00 H+0
ATOM 59 H 0 -7.298 -0.527 1.845 0.00 0.00 H+0
ATOM 60 H 0 -6.960 -1.721 3.122 0.00 0.00 H+0
ATOM 61 H 0 -6.012 -0.217 3.035 0.00 0.00 H+0
ATOM 62 H 0 -5.489 -3.250 0.063 0.00 0.00 H+0
ATOM 63 H 0 -6.655 -3.492 1.386 0.00 0.00 H+0
ATOM 64 H 0 -6.993 -2.299 0.109 0.00 0.00 H+0
ATOM 65 H 0 0.769 -1.121 -1.930 0.00 0.00 H+0
ATOM 66 H 0 2.187 -2.485 -2.032 0.00 0.00 H+0
ATOM 67 H 0 6.099 -1.229 -2.707 0.00 0.00 H+0
ATOM 68 H 0 7.231 0.823 -0.820 0.00 0.00 H+0
CONECT 1 2 39 40 41 NONE 73
CONECT 2 1 3 4 42 NONE 74
CONECT 3 2 43 44 45 NONE 75
CONECT 4 2 37 5 0 NONE 76
CONECT 5 4 31 6 0 NONE 77
CONECT 6 5 7 46 0 NONE 78
CONECT 7 6 8 9 0 NONE 79
CONECT 8 7 47 48 49 NONE 80
CONECT 9 7 10 29 0 NONE 81
CONECT 10 9 11 13 0 NONE 82
CONECT 11 10 17 12 0 NONE 83
CONECT 12 11 50 0 0 NONE 84
CONECT 13 10 14 15 0 NONE 85
CONECT 14 13 51 52 53 NONE 86
CONECT 15 13 16 54 0 NONE 87
CONECT 16 15 25 17 0 NONE 88
CONECT 17 16 11 18 0 NONE 89
CONECT 18 17 19 21 0 NONE 90
CONECT 19 18 20 55 0 NONE 91
CONECT 20 19 0 0 0 NONE 92
CONECT 21 18 22 23 0 NONE 93
CONECT 22 21 56 0 0 NONE 94
CONECT 23 21 24 25 0 NONE 95
CONECT 24 23 57 0 0 NONE 96
CONECT 25 23 16 26 0 NONE 97
CONECT 26 25 27 28 58 NONE 98
CONECT 27 26 59 60 61 NONE 99
CONECT 28 26 62 63 64 NONE 100
CONECT 29 9 30 31 0 NONE 101
CONECT 30 29 65 0 0 NONE 102
CONECT 31 29 5 32 0 NONE 103
CONECT 32 31 33 35 0 NONE 104
CONECT 33 32 34 66 0 NONE 105
CONECT 34 33 0 0 0 NONE 106
CONECT 35 32 36 37 0 NONE 107
CONECT 36 35 67 0 0 NONE 108
CONECT 37 35 4 38 0 NONE 109
CONECT 38 37 68 0 0 NONE 110
M END</inlineContents>
</jmolApplet>
</jmol>

= History =

In 1929, to investigate anecdotal evidence that families who cooked with crude cottonseed oil produced fewer children, a large scale Chinese fertility survey was carried out. The study concluded that it was this oil that affected male fertility, and it was determined that gossypol in the cotton seed oil could be used as a contraceptive. During the 1970s over 8,000 men were tested using this type of contraceptive and it was found that men taking a daily gossypol pill had reliable contraception. '[I'd like to see sources for the previous paragraph please]'

In late 2005, a team of researchers at Sunderland University found that gossypol has been seen to help stop the spread of psoriasis, a fairly common and unpleasant genetic skin condition, as well as reducing inflammation in sufferers. Psoriasis suffers have a genetic fault that means that under certain conditions their skin starts to produce far too many skin cells.

=Uses and side effects=
In 1970s, the Chinese proposed gossypol as a drug for male contraceptive use. Studies conducted by the International Organisation for Chemical Sciences in Development has shown that 40 of the 70 purified forms of gossypol were just as active as the original gossypol.<ref>http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=9639146&dopt=Citation</ref>

Among the side effects assiciated with the use of gossypol, the most serious was hypokalemic paralysis. Hypokalemic paralysis<ref>http://www.clevelandclinic.org/health/health-info/docs/2400/2452.asp?index=9499</ref> is also known as 'familial paralysis', and occurs due to low levels of potassium in the body. During an attack of paralysis, muscle weakness occurs in arms and legs. In more severe cases, this may also affect swallowing and breathing, which can be fatal.

Recovery of those who used gossypol is 75%; however, it can lead to other related symptoms such as smaller testicular colume, and elevated follicle stimulating hormone concentrations.

= Known hazards =

May be irritating to gastrointestinal tract. Large doses have caused edema of lungs, shortness of breath and paralysis in animals. Toxic to nonruminant animals such as humans, by reducing the capacity the blood has to carry oxygen.

A large-scale trial of gossypol was carried out in China. A high rate of hypokalemia was shown is test subjects.

A man who uses the drug for protracted periods could become partially, if not fully, infertile.

= References =
<references/>

*http://www.emolecules.com/cgi-bin/more?vid=538892#

*The Merck Index- An Encylopedia of Chemicals, Drugs and Biologicals, Thirteenth edition, Merck & Co., Inc.

*http://news.bbc.co.uk/1/hi/england/wear/4284602.stm

*http://www.malecontraceptives.org/methods/gossypol.php