Novel Michael Addition Products of Bis(amino acidato)metal(II) Complexes: Synthesis, Characterization, Dye Degradation, and Oxidation Properties

Michael addition reactions of bis(amino acidato)metal(II) complexes (metal = copper, nickel, zinc; amino acid = glycine, dl-alanine, l-alanine) with acrylonitrile have been carried out under various experimental conditions in the absence of a base, resulting in mono- and disubstituted products in hi...

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Bibliographic Details
Published in:Inorganic chemistry 2008-07, Vol.47 (13), p.5821-5830
Main Authors: Rajalakshmi, V, Vijayaraghavan, V. R, Varghese, Babu, Raghavan, A
Format: Article
Language:English
Subjects:
Amino acids
Catalysis
Coloring Agents - chemistry
Coordination compounds
Degradation
Dyes
Electron paramagnetic resonance
Nitrogen atoms
Organometallic Compounds - chemical synthesis
Organometallic Compounds - chemistry
Oxidation
Oxidation-Reduction
Spectrum Analysis
X-Ray Diffraction
Zinc
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Summary:Michael addition reactions of bis(amino acidato)metal(II) complexes (metal = copper, nickel, zinc; amino acid = glycine, dl-alanine, l-alanine) with acrylonitrile have been carried out under various experimental conditions in the absence of a base, resulting in mono- and disubstituted products in high yield, including partially hydrolyzed products. A reaction mechanism for the Michael addition on the nitrogen atom of the coordinated amino acid moiety, replacing the amino hydrogen atom(s), is proposed. All of the products have been characterized by Fourier transform infrared spectroscopy, electron paramagnetic resonance spectra, and elemental and electrochemical analyses. The single-crystal structures of bis(N-cyanoethylglycinato)copper(II) monohydrate (1a), diaquabis(N-cyanoethylglycinato)nickel(II), aquabis(N,N-dicyanoethylglycinato)copper(II) (2a), and bis[(N-propionamido-N-cyanoethyl)glycinato]copper(II) dihydrate (4a) have been confirmed by X-ray diffraction techniques. The products 1a, 2a, 4a, and bis(N-propionamidoglycinato)copper(II) monohydrate (3a) have been used as catalysts for the degradation of a phenol red dye and mild oxidation of various organic substrates in the presence of hydrogen peroxide. The monosubstituted complexes have been found to catalyze the reactions to a greater extent than the disubstituted complexes.
ISSN:0020-1669
1520-510X
DOI:10.1021/ic800086y