Synthesis and Structure of Tetra- and Triphenylantimony Organosulfonates

Abstract

Tetraphenylantimony 2-naphthalenesulfonate (I), tetraphenylantimony phenylmethanesulfonate (II), and bis(tetraphenylantimony) sulfate (III) were synthesized via reaction of pentaphenylantimony with 2-naphthalenesulfonic acid, triphenylantimony bis(phenylmethanesulfonate), and triphenylantimony sulfate, respectively, in toluene. Triphenylantimony bis(phenylmethanesulfonate) (IV) was synthesized from triphenylstibine, phenylmethanesulfonic acid, and hydrogen peroxide (taken in the molar ratio of 1 : 2 : 1). Organoantimony betaine \(Ph_3 \mathop {Sb}\limits^ + CH(Ph)SO_2 \bar O \left( V \right)\) (V) was obtained by reacting triphenylstibine with phenylmethanesulfonyl chloride in the presence of hydrogen peroxide. The structures of the compounds synthesized were determined using X-ray diffraction analysis. The Sb atoms in I–IV have distorted trigonal bipyramidal coordination. The Sb–C and Sb–O distances are equal to 2.100(4)–2.140(3) and 2.644(2) A in molecule I, 2.105(2)–2.131(2) and 2.699(1) A in II, 2.096(6)–2.169(6) and 2.101(6), 2.271(3) A in III, and 2.101(3)–2.102(5) and 2.111(2) A in IV. In V, the Sb atoms have close tetrahedral (2.105–2.115 A) and remote (2.65, 3.019 A) octahedral environment (the oxygen atoms of sulfo group of their own and neighboring molecules). Two betaine molecules are joined through the O atoms of the sulfo groups of bidentate phenylmethanesulfonate ligands to form a centrosymmetrical dimer. The intermolecular C(1)–H(1)···O(1) hydrogen bonds (3.10 A) are formed that strengthen the dimer.