Lithium diphenylphosphide
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| Preferred IUPAC name
Lithium diphenylphosphanide | |
| Identifiers | |
3D model (JSmol)
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C12H10LiP | |
| Molar mass | 192.13 g·mol−1 |
| Appearance | pale yellow solid |
| Reacts with water | |
| Solubility | Ethers, hydrocarbons |
| Hazards | |
| GHS labelling: | |
  
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| Danger | |
| H302, H312, H314, H332, H410 | |
| P260, P261, P264, P270, P271, P273, P280, P301+P312, P301+P330+P331, P302+P352, P303+P361+P353, P304+P312, P304+P340, P305+P351+P338, P310, P312, P321, P322, P330, P363, P391, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Lithium diphenylphosphide contains lithium and the organophosphorus anion with the formula (C6H5)2PLi. It is a red, air-sensitive solid that is used in the preparation of diphenylphosphino compounds.
Synthesis and reactions
[edit]The lithium, sodium, and potassium salts are prepared by reduction of chlorodiphenylphosphine,[1] triphenylphosphine,[2][3] or tetraphenyldiphosphine with alkali metals (M):
- (C6H5)2PCl + 2 M → (C6H5)2PM + MCl
- (C6H5)3P + 2 M → (C6H5)2PM + MC6H5
- (C6H5)4P2 + 2 M → 2 (C6H5)2PM
They can also be obtained by deprotonation of diphenylphosphine.
With water, the salts convert to diphenylphosphine:[3]
- (C6H5)2PLi + H2O → (C6H5)2PH + LiOH
With halocarbons, the salts react to give tertiary phosphines:[4]
- (C6H5)2PM + RX → (C6H5)2PR + MX
When treated with metal halides, lithium diphenylphosphide gives transition metal phosphido complexes.
Structure and physical properties
[edit]Although treated as salts, alkali diphenylphosphides are highly aggregated in solution. They adopt polymeric structures as solids.
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Part of the polymeric structure of LiPPh2(Et2O).[5]
As an ether complex, the lithium salt is dark red.[6]
Related compounds
[edit]- Sodium diphenylphosphide (CAS RN 4376-01-6)
- Potassium diphenylphosphide (CAS RN 15475-27-1)
References
[edit]- ^ Goldsberry, R.; Cohn, Kim; Hawthorne, M. F.; Dunks, G. B.; Wilson, R. J. (1972). "Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine". In Cotton, F. A. (ed.). Inorganic Syntheses. Vol. 13. pp. 26–32. doi:10.1002/9780470132449.ch7. ISBN 9780470132449.
- ^ Luther, George W. III; Beyerle, Gordon; Cox, Daniel; Cohn, Kim (1977). "Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine". In MacDiarmid, Alan G. (ed.). Inorganic Syntheses. Vol. 17. pp. 186–188. doi:10.1002/9780470132487.ch51. ISBN 9780470132487.
- ^ a b Bianco, V. D.; Doronzo, S.; Chan, J.; Bennett, M. A. (1976). "Diphenylphosphine". In Basolo, Fred (ed.). Inorganic Syntheses. Vol. 16. pp. 161–188. doi:10.1002/9780470132470.ch43. ISBN 9780470132470.
- ^ Levason, W.; Mcauliffe, C. A.; Barth, R. C.; Grim, S. O. (1976). "Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine". In Basolo, Fred (ed.). Inorganic Syntheses. Vol. 16. pp. 188–192. doi:10.1002/9780470132470.ch50. ISBN 9780470132470.
- ^ Bartlett, Ruth A.; Olmstead, Marilyn M.; Power, Philip P. (1986). "Structural Characterization of the Solvate Complexes of the Lithium Diorganophosphides [{Li(Et2O)PPh2}∞], [{Li(THF)2PPh2}∞], and [{Li(THF)P(C6H11)2}∞]". Inorg. Chem. 25: 1243–1247. doi:10.1021/ic00228a034.
- ^ Hegedüs, Kristof (12 Dec 2012). "The reaction of triphenylphosphine with lithium..." Pictures from an Organic Chemistry Laboratory. Tumblr. Archived from the original on 12 November 2020. Retrieved 6 January 2025.
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