Synthesis and Structure of Tetraphenylantimony Nicotinate

Tetraphenylantimony nicotinate was prepared in 91% yield by reaction of pentaphenylantimony with triphenylantimony bis(nicotinate) in toluene. Triphenylantimony bis(nicotinate), in turn, was prepared in 87% yield by oxidative addition of pyridine-3-carboxylic acid to triphenylstibine in ether in the presence of hydrogen peroxide. The structure of tetraphenylantimony nicotinate was determined by single-crystal X-ray diffraction. The Sb atom has a distorted trigonal bipyramidal coordination surrounding with the carboxy group in the axial position. The Sb-C distances are 2.118(1), 2.121(1), 2.130(1), and 2.170(1) Å, and the Sb-O distance is 2.268(1) Å. There is an intramolecular contact between the Sb atom and the carbonyl O atom [3.363(1) Å].