Synthesis, Spectroscopic Characterization: (IR, Multinuclear NMR, 119mSn Mössbauer and Mass Spectrometry), and Biological Activity (Antibacterial, Antifungal, and Cytotoxicity) of Di‐ and Triorganotin(IV) Complexes of (E)‐3‐(4‐Chlorophenyl)‐2‐phenylpropenoic Acid

Abstract

In an effort to develop new organotin(IV) compounds of industrial and biological importance, a series of di‐ and triorganotin(IV) complexes of (E)‐3‐(4‐chlorophenyl)‐2‐phenylpropenoic acid with the general formula R4‐n SnL n have been synthesized by the reaction of the corresponding organotin chlorides with the sodium salt of (E)‐3‐(4‐chlorophenyl)‐2‐phenylpropenoic acid (C15H10ClO2Na) where, R = CH3, C2H5, n‐C4H9, C6H5, C6H5 · CH2, n = 1 or 2 and L = acid anion (C15H10ClO2 −). The dimeric tetraorganodicarboxylatodistannoxanes [(Me2SnL)2O]2 compound (2) and [(Bu2SnL)2O]2 compound (4), L = C15H10ClO2 −, were synthesized by the reaction of R2SnO with the ligand acid (HL) in 1:1 molar ratio with azeotropic removal of water. The structures of the complexes are discussed on the basis of IR, multinuclear (1H, 13C, 119Sn) NMR, 119mSn Mössbauer spectroscopies and mass spectrometry. The spectroscopic results substantiate that all the diorganotin(IV) derivatives possess trigonal‐bipyramidal structures in solution and octahedral geometry in the solid state. A linear polymeric trigonal‐bipyramidal structure in the solid state and a tetrahedral environment around the tin atom in non‐coordinating solvents has been proposed for the triorganotin(IV) derivatives. The Δν [Δν = νasym(COO) − νsym(COO)] values obtained from the IR data, in comparison to the ligand acid and its sodium salt, fall in the range which shows that the ligand may act as a bidentate coordinating group through the carboxyl (COO) oxygen atoms. The biological activity and LD50 data of the synthesized compounds are also reported. The triorganotin(IV) complexes exhibit significantly better activities than the diorganotin(IV) derivatives. The LD50 data show that most of the investigated compounds are cytotoxic.