Tri-para-tolylantimony bis(3-nitrobenzoate) (I), tri-para-tolylantimony bis(3,5-dinitrobenzoate) (II), and tri-para-tolylantimony bis(bromoacetate) (III), in which the Sb atoms have a trigonal bipyramidal coordination according to X-ray diffraction analysis, have been synthesized by the reaction of tri-para-tolylantimony (4-MeC6H4)(3)Sb with 3-nitrobenzoic, 3,5-dinitrobenzoic, and bromoacetic acids in the presence of tert-butyl hydroperoxide. The OSbO axial angles are 171.83(12)degrees, 173.06(9)degrees, and 173.82(10)degrees. The Sb-O and Sb-C bond lengths are 2.109(3), 2.123(3), and 2.095(4)-2.111(5) angstrom in I, 2.108(2), 2.133(3), and 2.095(4)2.103(3) angstrom in II, 2.126(3), 2.133(3), and 2.102(3)-2.115(3) angstrom in III. The Sb...O intramolecular distances (3.105(5), 3.168(5) in I, 3.060(4), 3.096(4) in II, 3.069(4), 3.100(4) angstrom in III) are similar to 0.5 angstrom smaller than the sum of the antimony and oxygen van der Waals radii.