New diorganotin(IV) complexes with 3-(2-hydroxy-5-methylphenylamino)-1,3-diphenylprop-2-en-1-one: Synthesis, spectroscopic characterization, structural studies and antibacterial activity

Abstract

New organotin(IV) complexes, Ph2SnL (1) and Me2SnL (2), have been synthesized from reaction of corresponding diorganotin(IV) dichlorides with a Schiff base, 3-(2-hydroxy-5-methylphenylamino)-1,3-diphenylprop-2-en-1-one (H2L), derived from condensation of 2-amino-4-methylphenol with dibenzoylmethane. The synthesized compounds have been investigated by elemental analysis and IR, 1H NMR, and 119Sn NMR spectroscopy. Spectroscopic studies show that the Schiff base acts as a tridentate dianionic ligand and coordinates via the nitrogen and phenolic and enolic oxygen atoms. The structures of H2L and 2 have been also confirmed by X-ray crystallography. Schiff base exists as the keto-amine tautomeric form in solid state with two intramolecular hydrogen bonds of the NH⋯O type and also intermolecular hydrogen bonds of OH⋯O type that create a dimer. In the structure of 2, tin center is surrounded by two O and one N atoms from the ligand and two C atoms of methyl groups and the sixth coordination site is occupied by phenolic oxygen atom of another molecule, thus a dimeric molecule with a Sn2O2 four-membered ring is formed. The in vitro antibacterial activity of ligand and complexes has been evaluated against Gram-positive (Bacillus cereus and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria. H2L showed no activity but the diphenyltin(IV) complex exhibited good activities along with the standard antibacterial drugs.