Lithium diphenylphosphide
LiPPh2.png
Names
Preferred IUPAC name
Lithium diphenylphosphanide
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C12H10P.Li/c1-3-7-11(8-4-1)13-12-9-5-2-6-10-12;/h1-10H;/q-1;+1
    Key: WKUYEGHEUWHKIU-UHFFFAOYSA-N
  • [Li+].C1=CC=C(C=C1)[P-]C2=CC=CC=C2
Properties
C12H10LiP
Molar mass 192.13 g·mol−1
Appearance pale yellow solid
Reacts with water
Solubility Ethers, hydrocarbons
Hazards
GHS labelling:
GHS05: Corrosive
GHS07: Exclamation mark
GHS09: Environmental hazard
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).

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.

Part of the polymeric structure of LiPPh2(Et2O).[1]
Part of the polymeric structure of LiPPh2(Et2O).[1]

Synthesis and reactions

The lithium, sodium, and potassium salts are prepared by reduction of chlorodiphenylphosphine,[2] triphenylphosphine,[3][4] 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:[4]

(C6H5)2PLi + H2O → (C6H5)2PH + LiOH

With halocarbons, the salts react to give tertiary phosphines:[5]

(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.

Related compounds

References

  1. ^ Ruth A. Bartlett, Marilyn M. Olmstead, Philip P. Power (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.((cite journal)): CS1 maint: uses authors parameter (link)
  2. ^ R. Goldsberry Kim Cohn (1972). "Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)-phosphine". Diphenyl(trimethylsilyl)phosphine and Dimethyl(trimethylsilyl)‐phosphine. Inorganic Syntheses. Vol. 13. pp. 26–32. doi:10.1002/9780470132449.ch7. ISBN 9780470132449.((cite book)): CS1 maint: uses authors parameter (link)
  3. ^ George W. Luther, III, Gordon Beyerle (1977). "Lithium Diphenylphosphide and Diphenyl(Trimethylsilyl)Phosphine". Inorganic Syntheses. Inorganic Syntheses. Vol. 17. pp. 186–188. doi:10.1002/9780470132487.ch51. ISBN 9780470132487.((cite book)): CS1 maint: uses authors parameter (link)
  4. ^ a b V. D. Bianco, S. Doronzo (1976). "Diphenylphosphine". Inorganic Syntheses. Inorganic Syntheses. Vol. 16. pp. 161–188. doi:10.1002/9780470132470.ch43. ISBN 9780470132470.((cite book)): CS1 maint: uses authors parameter (link)
  5. ^ W. Levason, C. A. Mcauliffe (1976). "Cis -2-Diphenylarsinovinyldiphenylphosphine and 2-Diphenylarsinoethyldiphenylphosphine". Cis‐2‐Diphenylarsinovinyldiphenylphosphine and 2‐Diphenylarsinoethyldiphenylphosphine. Inorganic Syntheses. Vol. 16. pp. 188–192. doi:10.1002/9780470132470.ch50. ISBN 9780470132470.((cite book)): CS1 maint: uses authors parameter (link)