Synthesis and structural and electrochemical characterization of novel macrocyclic vic-dioxime ligand and its mononuclear transition and nontransition metal complexes

摘要

The reaction of N-(4-aminophenyl)aza-15-crown-5 (1) with anti-chlorophenylglyoxime (2) produces a novel azacrown ether containing wc-dioxime, N-(4-aminophenyl)aza-15-crown-5-phenylgryoxime (LH2). LH2 reacts with Ni(II), Cu(II), Co(II), Cd(II), and Zn(II) ions to yield the mononuclear transition and non-transition metal complexes [M(LH) 2 ] (M = Ni and Cu), [M(LH)2(H2O)2] (M = Co), and [M(LH)(H2O)(C1)] (M = Cd and Zn). The structural features of LH2 were studied using several techniques including, elemental analysis, Fourier transform infrared spectroscopy (FT-IR), ultraviolet visible (UV-Vis), mass spectrometry (MS), 1-dimensional (ID) ~1H-NMR and ~(13)CNMR, distortionless enhancement by polarization transfer (DEPT) 2-dimensional (2D) heteronuclear single-quantum coherence (HSQC), and heteronuclear multiple-bond correlation (HMBC) techniques. The structures of the complexes were confirmed by elemental analyses and with the use of magnetic susceptibility measurements, MS, UV-Vis, FT-IR, ~1H-NMR, and ~(13)C-NMR techniques. The redox behaviors of the ligand and its complexes were verified with cyclic voltammetry (CV) at a glassy carbon (GC) electrode in 0.1 M tetrabutylammoniumtetrafmoroborate (TBATFB) in dimethyl sulfoxide (DMSO).