Lithium diphenylphosphide
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Preferred IUPAC name Lithium diphenylphosphanide | |
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Properties | |
Chemical formula | C12H10LiP |
Molar mass | 192.13 g·mol−1 |
Appearance | pale yellow solid |
Solubility in water | Reacts with water |
Solubility | Ethers, hydrocarbons |
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Danger | |
Hazard statements | H302, H312, H314, H332, H410 |
Precautionary statements | 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). Infobox references |
Lithium diphenylphosphide contains lithium and the organophosphorus anion with the formula (C6H5)2PLi. It is an air-sensitive solid that is used in the preparation of diphenylphosphino compounds. As an ether complex, the lithium salt is dark red.
Synthesis and reactions
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
Although treated as salts, alkali diphenylphosphides are highly aggregated in solution. They adopt polymeric structures as solids.
- Part of the polymeric structure of LiPPh2(Et2O).[5]
Related compounds
- Sodium diphenylphosphide (CAS RN 4376-01-6)
- Potassium diphenylphosphide (CAS RN 15475-27-1)
References
- ^ 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.
- v
- t
- e
- Li2
- LiAlCl4
- Li1+xAlxGe2−x(PO4)3
- LiAlH4
- LiAlO2
- LiAl1+xTi2−x(PO4)3
- LiAs
- LiAsF6
- Li3AsO4
- LiAt
- Li[AuCl4]
- LiB(C2O4)2
- LiB(C6F5)4
- LiBF4
- LiBH4
- LiBO2
- LiB3O5
- Li2B4O7
- Li2TiF6
- Li2ZrF6
- Li2B4O7·5H2O
- LiBSi2
- LiBr
- LiBr·2H2O
- LiBrO
- LiBrO2
- LiBrO3
- LiBrO4
- Li2C2
- LiCF3SO3
- CH3CH(OH)COOLi
- LiC2H2ClO2
- LiC2H3IO2
- Li(CH3)2N
- LiCHO2
- LiCH3O
- LiC2H5O
- LiCN
- Li2CN2
- LiCNO
- Li2CO3
- Li2C2O4
- LiCl
- LiCl·H2O
- LiClO
- LiFO
- LiClO2
- LiClO3
- LiClO4
- LiCoO2
- Li2CrO4
- Li2CrO4·2H2O
- Li2Cr2O7
- CsLiB6O10
- LiD
- LiF
- Li2F
- LiF4Al
- Li3F6Al
- FLiBe
- LiFePO4
- FLiNaK
- LiGaH4
- Li2GeF6
- Li2GeO3
- LiGe2(PO4)3
- LiH
- LiH2AsO4
- Li2HAsO4
- LiHCO3
- Li3H(CO3)2
- LiH2PO3
- LiH2PO4
- LiHSO3
- LiHSO4
- LiHe
- LiI
- LiIO
- LiIO2
- LiIO3
- LiIO4
- Li2IrO3
- Li7La3Zr2O12
- LiMn2O4
- Li2MoO4
- Li0.9Mo6O17
- LiN3
- Li3N
- LiNH2
- Li2NH
- LiNO2
- LiNO3
- LiNO3·H2O
- Li2N2O2
- LiNa
- Li2NaPO3
- LiNaNO2
- LiNbO3
- Li2NbO3
- LiO−
- LiO2
- LiO3
- Li2O
- Li2O2
- LiOH
- Li3P
- LiPF6
- Li3PO4
- Li2HPO3
- Li2HPO4
- Li3PO3
- Li3PO4
- Li2Po
- Li2PtO3
- Li2RuO3
- Li2S
- LiSCN
- LiSH
- LiSO3F
- Li2SO3
- Li2SO4
- Li[SbF6]
- Li2Se
- Li2SeO3
- Li2SeO4
- LiSi
- Li2SiF6
- Li4SiO4
- Li2SiO3
- Li2Si2O5
- LiTaO3
- Li2Te
- LiTe3
- Li2TeO3
- Li2TeO4
- Li2TiO3
- Li4Ti5O12
- LiTi2(PO4)3
- LiVO3·2H2O
- Li3V2(PO4)3
- Li2WO4
- LiYF4
- LiZr2(PO4)3
- Li2ZrO3
- Hemolithin (extraterrestrial protein)
- Organolithium reagents
- CH3COOLi
- C4H6LiNO4
- LiC2F6NO4S2
- LiN(SiMe3)2
- Li3C6H5O7
- C5H5Li
- LiN(C3H7)2
- (C6H5)2PLi
- C18H35LiO3
- C6H13Li
- C4H9Li
- CH3CHLiCH2CH3
- (CH3)3CLi
- C12H28BLi
- CH3Li
- Li+C10H8−
- C5H11Li
- C5H3LiN2O4
- C6H5Li
- LiC2CH3
- LiO2C(CH2)16CH3
- C4H5LiO4
- LiEt3BH
- LiOC(CH3)3
- C9H18LiN
- LiC2H3 Vinyllithium
- LiC
11H
23COO
- Amblygonite
- Berezanskite
- Brannockite
- Cryolithionite
- Darapiosite
- Darrellhenryite
- Elbaite
- Fluorine Elbaite
- Fluor-liddicoatite
- Emeleusite
- Eucryptite LiAlSiO4
- Faizievite
- Hectorite
- Hsianghualite
- Jadarite LiNaSiB3O7OH
- Keatite Li(AlSi2O6)
- Kunzite
- Lavinskyite
- Lepidolite
- Lithiophilite LiMnPO4
- Lithiophosphate Li3PO4
- Manandonite
- Manganoneptunite
- Nambulite
- Neptunite
- Olympite
- Petalite LiAlSi4010
- Pezzottaite Cs(Be2Li)Al2Si6O18
- Rossmanite
- Saliotite
- Sogdianite
- Spodumene LiAl(SiO3)2
- Sugilite
- Tiptopite
- Tourmaline
- Triphylite LiFePO4
- Zabuyelite Li2CO3
- Zektzerite
- Zinnwaldite
- LixBey
- HLiHe+
- LiFHeO
- LiHe2
- (HeO)(LiF)2
- La2/3-xLi3xTiO3He
- Aluminium–lithium alloys
- Heteroatom-promoted lateral lithiation
- LB buffer
- Lithium atom
- Lithium medication
- LiNixCoyAlzO2
- LiNixMnyCozO2
- Lithium soap
- Lithium Triangle
- Lucifer yellow
- Magnesium–lithium alloys
- NASICON
- Environmentally friendly red light flare