Phosphoranes: Difference between revisions
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[[File:Phosphorane.svg|thumb|right|The structure of a typical phosphorane group.]] |
[[File:Phosphorane.svg|thumb|right|The structure of a typical phosphorane group.]] |
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A '''phosphorane''' ([[IUPAC]] name: ''' |
A '''phosphorane''' ([[IUPAC]] name: ''' |
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Phosphoranes of the type PX<sub>5</sub> adopt a [[trigonal bipyramidal molecular geometry]] with the two [[apical (chemistry)|apical]] bonds longer than the three equatorial bonds. [[Hypervalent molecule|Hypervalent bonding]] is described by inclusion of non-bonding MOs, as also invoked for the closely related molecule [[phosphorus pentafluoride]].<ref>G. L. Miessler and D. A. Tarr “Inorganic Chemistry” 3rd Ed, Pearson/Prentice Hall publisher, {{ISBN|0-13-035471-6}}.</ref> |
Phosphoranes of the type PX<sub>5</sub> adopt a [[trigonal bipyramidal molecular geometry]] with the two [[apical (chemistry)|apical]] bonds longer than the three equatorial bonds. [[Hypervalent molecule|Hypervalent bonding]] is described by inclusion of non-bonding MOs, as also invoked for the closely related molecule [[phosphorus pentafluoride]].<ref>G. L. Miessler and D. A. Tarr “Inorganic Chemistry” 3rd Ed, Pearson/Prentice Hall publisher, {{ISBN|0-13-035471-6}}.</ref> |
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==Examples== |
==Examples== |
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The parent [[hydride]] compound is the hypothetical molecule PH<sub>5</sub>. |
The parent [[hydride]] compound is the hypothetical molecule PH<sub>5</sub>. |
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[[Pentaphenylphosphorane]] (Ph<sub>5</sub>P) is stable.<ref>{{Note|Quin}} ''A Guide to Organophosphorus Chemistry'' Louis D. Quin '''2000''' John Wiley & Sons {{ISBN|0-471-31824-8}}</ref> |
[[Pentaphenylphosphorane]] (Ph<sub>5</sub>P) is stable.<ref>{{Note|Quin}} ''A Guide to Organophosphorus Chemistry'' Louis D. Quin '''2000''' John Wiley & Sons {{ISBN|0-471-31824-8}}</ref> |
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== References == |
== References == |
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{{Reflist}} |
{{Reflist}} |
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{{Authority control}} |
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[[Category:Organophosphanes]] |
[[Category:Organophosphanes]] |
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Latest revision as of 16:10, 19 October 2023
A phosphorane (IUPAC name:
Phosphoranes of the type PX5 adopt a trigonal bipyramidal molecular geometry with the two apical bonds longer than the three equatorial bonds. Hypervalent bonding is described by inclusion of non-bonding MOs, as also invoked for the closely related molecule phosphorus pentafluoride.[1]
Examples
[edit]The parent hydride compound is the hypothetical molecule PH5.
Pentaphenylphosphorane (Ph5P) is stable.[2]
Pentaalkoxyphosphoranes are more common with electronegative substituents. Examples of P(OR)5 (R = alkyl), have however been prepared by reaction of phosphites with benzene alkyl sulfenates:[3]
- P(OR)3 + 2 ROSC6H5 → P(OR)5 + (SC6H5)2
Wittig reagents
[edit]Phosphoranes of the type R3P=CR2 are more common and more important. Phosphoranes are also considered to be one of the resonance structures of ylides, these compounds feature a tetrahedral phosphorus center including a phosphorus–carbon double bond. These compounds are used as reagents in the Wittig reaction, for instance methylenetriphenylphosphorane or Ph3P=CH2.
See also
[edit]References
[edit]- ^ G. L. Miessler and D. A. Tarr “Inorganic Chemistry” 3rd Ed, Pearson/Prentice Hall publisher, ISBN 0-13-035471-6.
- ^ ^ A Guide to Organophosphorus Chemistry Louis D. Quin 2000 John Wiley & Sons ISBN 0-471-31824-8
- ^ Chang, Lydia L.; Denney, Donald B.; Denney, Dorothy Z.; Kazior, Richard J. (1977). "Some acyclic pentaalkoxyphosphoranes". Journal of the American Chemical Society. 99 (7): 2293–2297. doi:10.1021/ja00449a044.
