Synthesis and X-ray powder diffraction, electrochemical, and genotoxic properties of a new azo-Schiff base and its metal complexes

A new, substituted 2-[(E) -f[4-(benzyloxy)phenyl]iminog methyl]-4-[(E)-(4-nitrophenyl)diazenyl]phenol azoazomethine ligand (mbH) was synthesized from 2-hydroxy-5-[(4-nitrophenyl)diazenyl]benzaldehyde and 4-benzyloxyanilinehydrochloride in ethyl alcohol solution. These mononuclear Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes of the ligand were prepared and their structures were proposed by elemental analysis, and infrared and ultraviolet-visible spectroscopy; the proton NMR spectrum of the mbH ligand was also recorded. The azo-azomethine ligand, mbH, behaves as a bidentate ligand coordinating through the nitrogen atom of the azomethine (-CH=N-) and the oxygen atom of the phenolic group. Elemental analyses indicated that the metal:ligand ratio was 1:2 in the metal chelates. Powder X-ray diffraction parameters suggested a monoclinic system for the mbH ligand and its Ni(II), Cu(II), Co(II), and Zn(II) complexes, and an orthorhombic system for the Mn(II) complex. Electrochemical properties of the ligand and its metal complexes were investigated in 1 × 10-3 -1 × 10-4 M DMF and CH3CN solvent in the range 200, 250, and 500 mV s-1 scan rates. The ligand showed both reversible and irreversible processes at these scan rates. In addition, genotoxic properties of the ligand and its complexes were examined. © Tubitak