Cd(II) and Cu(II) complexes of polydentate Schiff base ligands: synthesis, characterization, properties and biological activity

Abstract

We report the synthesis of the Schiff base ligands, 4-[(4-bromo-phenylimino)-methyl]-benzene-1,2,3-triol (A 1), 4-[(3,5-di- tert-butyl-4-hydroxy-phenylimino)-methyl]-benzene-1,2,3-triol (A 2), 3-( p-tolylimino-methyl)-benzene-1,2-diol (A 3), 3-[(4-bromo-phenylimino)-methyl]-benzene-1,2-diol (A 4), and 4-[(3,5-di- tert-butyl-4-hydroxy-phenylimino)-methyl]-benzene-1,3-diol (A 5), and their Cd(II) and Cu(II) metal complexes, stability constants and potentiometric studies. The structure of the ligands and their complexes was investigated using elemental analysis, FT-IR, UV–Vis, 1H and 13C NMR, mass spectra, magnetic susceptibility and conductance measurements. In the complexes, all the ligands behave as bidentate ligands, the oxygen in the ortho position and azomethine nitrogen atoms of the ligands coordinate to the metal ions. The keto-enol tautomeric forms of the Schiff base ligands A 1–A 5 have been investigated in polar and non-polar organic solvents. Antimicrobial activity of the ligands and metal complexes were tested using the disc diffusion method and the strains Bacillus megaterium and Candida tropicalis. Protonation constants of the triol and diol Schiff bases and stability constants of their Cu 2+ and Cd 2+ complexes were determined by potentiometric titration method in 50% DMSO–water media at 25.00 ± 0.02 °C under nitrogen atmosphere and ionic strength of 0.1 M sodium perchlorate. It has been observed that all the Schiff base ligands titrated here have two protonation constants. The variation of protonation constant of these compounds was interpreted on the basis of structural effects associated with the substituents. The divalent metal ions of Cu 2+ and Cd 2+ form stable 1:2 complexes with Schiff bases. The Schiff base complexes of cadmium inhibit the intense chemiluminescence reaction in dimethylsulfoxide (DMSO) solution between luminol and dioxygen in the presence of a strong base. This effect is significantly correlated with the stability constants K CdL of the complexes and the protonation constants K OH of the ligands; it also has a nonsignificant association with antibacterial activity.