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Lithium diphenylphosphide

From Wikipedia, the free encyclopedia
Lithium diphenylphosphide
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 mass192.13 g·mol−1
Appearancepale yellow solid
Reacts with water
SolubilityEthers, hydrocarbons
Hazards
GHS labelling:
GHS05: CorrosiveGHS07: Exclamation markGHS09: 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 theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Lithium diphenylphosphide contains lithium and theorganophosphorus 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

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The lithium, sodium, and potassium salts are prepared by reduction ofchlorodiphenylphosphine,[1]triphenylphosphine,[2][3] ortetraphenyldiphosphine 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 ofdiphenylphosphine.

With water, the salts convert todiphenylphosphine:[3]

(C6H5)2PLi + H2O → (C6H5)2PH + LiOH

Withhalocarbons, the salts react to give tertiary phosphines:[4]

(C6H5)2PM + RX → (C6H5)2PR + MX

When treated with metal halides, lithium diphenylphosphide givestransition 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.

  • Part of the polymeric structure of LiPPh2(Et2O).
    Part of the polymeric structure ofLiPPh2(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]
  1. ^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.
  2. ^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.
  3. ^abBianco, 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.
  4. ^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.
  5. ^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.
  6. ^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. Retrieved6 January 2025.{{cite web}}: CS1 maint: multiple names: authors list (link)
Inorganic (list)
Organic (soaps)
Minerals
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