Synthesis, characterization, HOMO–LUMO study, and antimicrobial activity of organotin(IV) complexes of 4-piperidine carboxamide and its Schiff base

Abstract

A series of organotin(IV) complexes has been synthesized by reacting 4-piperidine carboxamide with CS2 and R2SnCl2/R3SnCl in 1 : 1 M/L ratio at room temperature. The synthesized complexes were further treated with benzaldehyde to synthesize Schiff bases under stirring. All the complexes were characterized by elemental analysis, FT-IR, 1H and 13C NMR. FT-IR and semi-empirical study confirm the bidentate nature of ligand. The complexes exhibit four-coordinate geometry in solution. Thermodynamic parameters and molecular descriptors were calculated by using semi-empirical PM3 method. HOMO–LUMO calculations show that chlorodiorganotin complexes are more susceptible to nucleophilic attack when compared with triorganotin complexes. Negative heats of formation at 298 K demonstrate that 1, 4, and 7 are thermodynamically stable. The antimicrobial results have shown that complexes containing Schiff base exhibit significantly better activity compared to complexes with carboxamide derivatives.