Synthesis, structure, and antimicrobial activity of copper(II) chelates containing imidazole and condensation products of α-amino acids with salicylaldehyde and its derivatives

Abstract

Salicylaldehyde, 5-bromo- and 5-nitrosalicylaldehydes, 2-hydroxynaphthalene-1-carbaldehyde, and 2,3-, 2,4-, and 2,5-dihydroxybenzaldehydes reacted with glycine, alanine, and phenylalanine in ethanol in the presence of imidazole (Im) and copper(II) acetate hydrate to give copper(II) chelates with the composition Cu(Im)(L) · nH₂O (H₂L is the condensation product of the above aldehydes with α-amino acids; n = 0–2). The structure of the complex Cu(Im)(L¹) [H₂L¹ = 2-(2-hydroxybenzylideneamino)acetic acid] was determined by X-ray analysis. The crystalline structure of [2-(2-hydroxybenzylideneamino)acetato](imidazole)copper is formed by polymeric chains of the Cu(Im)(L¹) molecules linked through bridging oxygen atoms in the carboxy groups of the Schiff base ligand. The coordination unit has a distorted tetragonal pyramid configuration, where the pyramid base is composed of the phenol and carboxy oxygen atoms, CH=N nitrogen atom in the ligand H₂L¹ and imidazole nitrogen atom. The oxygen atom in the carboxy group in the neighboring molecule occupies the apical position of the coordination pyramid. The other coordination compounds also have polynuclear structure with the Schiff base H₂L acting as doubly deprotonated tridentate O,N,O-ligand and bridging carboxy groups. Thermal decomposition of the complexes includes their dehydration (70–95°C), while complete thermal decomposition occurs at 360–530°C. The synthesized complexes showed selective antimicrobial activity in the concentration range from 75 to 300 μg/ml against a number of standard strains of Staphylococcus aureus and Escherichia coli.