Tetradentate asymmetric Schiff bases and their Ni(II) and Fe(III) complexes

Abstract

Three asymmetric Schiff-base tetradentate diimines H2L1, H2L2, and H2L3 [(2-OH)C6H4N=CHC6H42-N=CHC6H3(2-OH)(5-X), X = H, CH3, Cl respectively] have been synthesized by a two step process. The reaction of 2-hydroxy aniline with 2-nitro-benzaldehyde in EtOH gave the starting Schiff base, 2-hydroxy-N-(2-nitrobenzylidene)aniline (SB-NO2), which was reduced into the amino derivative (SB-NH2) in solution. Reacting SB-NH2 with 2-hydroxybenzaldehyde, 2-hydroxy-5-methylbenzaldehyde and 2-hydroxy-5-chlorobenzaldehyde gave the three new ligands H2L1, H2L2, and H2L3 respectively. Their dimeric, binuclear metal complexes with Ni(II) and Fe(III) have also been synthesized. The ligands and their complexes were characterized by elemental analyses, LC–MS, IR, electronic, 1H and 13C-NMR spectra, TGA, conductivity and magnetic measurements. All of the spectroscopic, analytical and other data indicate octahedral geometry M2L2(H2O)X2 (M: Ni,Co;X: Cl or H2O), except for NiL2 which is monomeric. Antimicrobial activities of the ligands and the complexes were evaluated against five bacteria. While the ligands and the Ni complexes are inactive towards Pseudomonas aeruginosa and Staphylococcus aureus, Fe complexes are active; only Fe complexes are inactive against Escherichia coli. All of the compounds have antimicrobial activities against Bacillus subtilis, and Yersinia enterecolitica.