Triphenylstibine is the chemical compound with the formula Sb(C6H5)3, which is often abbreviated SbPh3, This colourless solid is a common organoantimony(III) compound. It serves as a ligand in coordination chemistry and as a reagent in organic synthesis.
Like the related molecules triphenylamine, triphenylphosphine and triphenylarsine, SbPh3 is pyramidal with a propeller-like arrangement of the phenyl groups. The Sb-C distances average 2.14-2.17 Å and the C-Sb-C angles are 95°.Adams, E. A.; Kolis, J. W.; Pennington, W. T. "Structure of Triphenylstibine" Acta Crystallographica 1990, volume C46, pp. 917-919.
Synthesis and reactions Triphenylstibine was first reported in 1886, being prepared from antimony trichloride and chlorobenzene: 6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl
In an alternative method, phenylmagnesium bromide is treated with SbCl3.
Upon treatment with antimony trichloride, triphenylstibine undergoes a redistribution reaction:
Stiboranes can be synthesised from triphenylstibine by halogenation:
As confirmed by X-ray crystallography, features pentacoordinate Sb(V) with trans-diaxial chloride ligands.
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