Pentaphenylantimony is an organoantimony compound containing five phenyl groups attached to one antimony atom. It has formula Sb(C6H5)5 (or SbPh5).
Structure The structure of pentaphenylantimony has been the subject of several studies, and a definite ground state remains uncertain. The molecule adopts a roughly square pyramidal shape in the unsolvated crystal. In crystals of the solvate with cyclohexane or tetrahydrofuran, the compound adopts a trigonal bipyramidal shape. When dissolved, molecules are also trigonal bipyramidal. According to solution NMR measurements, the phenyl groups all appear to be equivalent, indicating fluxionality. Solid pure pentaphenylantimony forms triclinic crystals in the P1 space group. The unit cell has a=10.286 b=10.600 and c=13.594 Å, α=79.20° β=70.43° γ=119.52°. The basal Sb-C bond length is 2.216 Å whereas the apex Sb-C length is 2.115 Å.
Reactions Pentaphenylantimony reacts with a variety of protic reagents (hydrogen halides, carboxylic acids, methanol, etc). Benzene is one product as well as a tetraphenylantimony(V) compound:
Ph5Sb + HOR → PhH + Ph4SbOR Ph5Sb + HX → PhH + Ph4SbX Halogens also cleave one Sb-phenyl bond:
Ph5Sb + X2 → Ph4SbX + PhX When heated, pentaphenylantimony forms triphenylstibine, biphenyl and p-quaterphenyl. A reaction with carbon tetrachloride yields tetraphenylstibonium chloride, chlorobenzene, and benzene. Some of these reactions may proceed by radical pathways.
Formation Pentaphenylantimony can be formed by reacting dichlorotriphenylantimony with phenyl lithium.
SbPh3Cl2 + 2 LiPh → SbPh5 + 2 LiCl
References
Further reading Smirnova, N.N.; Letyanina, I.A.; Larina, V.N.; Markin, A.V.; Sharutin, V.V.; Senchurin, V.S. (January 2009). "Thermodynamic properties of pentaphenylantimony Ph5Sb over the range from T→0K to 400K". The Journal of Chemical Thermodynamics. 41 (1): 46–50. doi:10.1016/j.jct.2008.08.002. Brock, C. P.; Ibers, J. A. (1976-01-01). "The role of crystal packing forces in the structure of pentaphenylantimony". Acta Crystallographica Section A. 32 (1): 38–42. Bibcode:1976AcCrA..32...38B. doi:10.1107/S0567739476000065.


