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Synthesis and characterization of mononuclear copper(II) complexes of pyridine 2-carboxamide: Their application as catalyst in peroxidative oxidation and antimicrobial agents

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Abstract

Four water soluble copper(II) complexes, [Cu(HL)2(H2O)2]Cl2 (1), [Cu(HL)2(ClO4)2] (2), [Cu(HL)2(SCN)2] (3) and [CuL2]⋅8H2O (4), where HL is pyridine 2–carboxamide, have been synthesized and characterized by various spectroscopic techniques. Structures have been determined by single crystal X-ray crystallography. The pH induced inter-conversion of Cu(HL)2(H2O)2]Cl2 (1) and [CuL2]⋅8H2O (4) through co-ordination mode switching was investigated thoroughly with the help of absorption spectroscopy. Complexes 1–3 were found to be active catalysts for the oxidation of toluene, ethyl benzene and cyclohexane in the presence of hydrogen peroxide as the oxidant under mild conditions. Toluene was oxidized to benzyl alcohol and benzaldehyde, ethyl benzene was oxidized to 1-phenylethanol and acetophenone and cyclohexane was oxidized to yield cyclohexanol and cyclohexanone Antimicrobial activities have been investigated with these copper(II) complexes against gram + ve bacteria, gram −ve bacterial and fungal species.

X-ray structural characterization, pH-induced co-ordination mode switching phenomenon, peroxidative oxidation catalysis and antimicrobial activity of water soluble, discrete mononuclear complexes of copper(II) using the simplest pyridine 2–carboxamide ligand (HL) and its deprotonated form have been investigated thoroughly.

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Acknowledgements

We gratefully acknowledge Dr. Papu Biswas for his help and suggestions during the course of this work and in the preparation of the manuscript. Authors also acknowledge DST-India for the Fast Track Project (No.SR/FT/CS-022/2009). S.S. is indebted to CSIR, India for his JRF [08/003(0083)/2011-EMR-1]. Thanks are due to the Department of Science and Technology, Government of India for establishing the National X-ray diffractometer facility at the Department of Inorganic Chemistry, Indian Association for the Cultivation of Science.

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Authors and Affiliations

  1. Department of Chemistry, Indian Institute of Engineering Science and Technology, Shibpur, Howrah, 711 103, India

    SUVENDU SAMANTA & SHOUNAK RAY

  2. Department of Biotechnology, Neotia Institute of Technology, Management and Science, Jhinga, Diamond Harbour Road, Amira, South 24 Parganas, 743 368, India

    SUTAPA JOARDAR

  3. Department of Chemistry, Nistarini College, Deshbandhu Road, Purulia, West Bengal, 723 101, India

    SUPRIYA DUTTA

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  1. SUVENDU SAMANTA
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Supplementary Information

ORTEP representations and H-bonding (Figures S1–S3), crystal packing views of 1–3 (Figure S4–S7), cyclic voltammograms of complexes 1–4 (Figure S8), potentiometric titration curve for the complex 1 (Figure S9), tables S1–S7, scheme S1, synthesis and characterization of the ligand HL, and crystal structure descriptions for complexes 1 and 3 are available at www.ias.ac.in/chemsci. CCDC-1011671(1), 1011672(2), 1011673(3) and 1011674(4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.

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SAMANTA, S., RAY, S., JOARDAR, S. et al. Synthesis and characterization of mononuclear copper(II) complexes of pyridine 2-carboxamide: Their application as catalyst in peroxidative oxidation and antimicrobial agents. J Chem Sci 127, 1451–1463 (2015). https://doi.org/10.1007/s12039-015-0909-8

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