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Triphenylstibine

Chemical compound From Wikipedia, the free encyclopedia

Triphenylstibine
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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[2] and as a reagent in organic synthesis.

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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°.[3]

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Synthesis and reactions

Triphenylstibine was first reported in 1886, being prepared from antimony trichloride and chlorobenzene:[4]

6 Na + 3 C6H5Cl + SbCl3 → (C6H5)3Sb + 6 NaCl

In an alternative method, phenylmagnesium bromide is treated with SbCl3.[5]

Upon treatment with antimony trichloride, triphenylstibine undergoes a redistribution reaction:[6]

Sb(C6H5)3 + 2SbCl3 → 3Sb(C6H5)Cl2

Stiboranes can be synthesised from triphenylstibine by halogenation:

Sb(C6H5)3 + Cl2 → Sb(C6H5)3Cl2

As confirmed by X-ray crystallography, Sb(C6H5)3Cl2 features pentacoordinate Sb(V) with trans-diaxial chloride ligands.[7]

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References

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