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Synthesis, characterization and antioxidant evaluation of metal complexes derived from a dianil ligand with a flexible linkage: anomalous magnetic behavior of the nickel complex

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Abstract

The synthesis and characterization of N,N′-bis (1-naphthaldimine)-p-oxydianiline, H2L, and its Zn(II), Cu(II), Ni(II) and Co(II) complexes are reported. Single crystal X-ray structural analysis showed that H2L consists of two tautomers where the central diphenylether unit is flanked by either two ketoamino forms or by one ketoamino and one enolimino form. Physico-chemical data revealed the formation of non-electrolytic [M2L2(2H2O) n ]·mH2O (n and m = 0–2) complexes with variable geometries. The nickel complex exhibited anomalous magnetic behavior compared to literature analogues. This result is attributed to molecular association and suggests the existence of both planar and octahedral forms in a conformational equilibrium. These complexes exhibit thermal stability up to 700 °C, except for the Ni(II) complex which degraded to its oxide. Antimicrobial screening data showed that H2L had no efficacy against a panel of pathogenic microorganisms, whereas the Ni(II) complex exhibited potency both as an antibacterial and antifungal agent. The properties of the complexes with respect to DPPH radical scavenging, acetyl cholinesterase inhibition and antihemolytic activity were evaluated.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321, Egypt

    Amel F. Elhusseiny, Hammed H. A. M Hassan & Ali El-Dissouky

  2. Department of Pharmacology and Toxicology, Faculty of Pharmacy, Pharos University, Canal El Mahmoudia Street, Beside Green Plaza Complex, Alexandria, 21311, Egypt

    Hend Hussien

  3. Department of Crystallography, Biochemical Sciences, Birkbeck College, Malet Street, London, WC1E 7HX, UK

    Rex A. Palmer

  4. Christopher Ingold Laboratories, Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, UK

    Jeremy K. Cockcroft

Authors
  1. Amel F. Elhusseiny
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  2. Hammed H. A. M Hassan
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  3. Hend Hussien
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  4. Ali El-Dissouky
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  5. Rex A. Palmer
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  6. Jeremy K. Cockcroft
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Correspondence to Amel F. Elhusseiny.

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Elhusseiny, A.F., M Hassan, H.H.A., Hussien, H. et al. Synthesis, characterization and antioxidant evaluation of metal complexes derived from a dianil ligand with a flexible linkage: anomalous magnetic behavior of the nickel complex. Transition Met Chem 40, 643–655 (2015). https://doi.org/10.1007/s11243-015-9958-6

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  • DOI: https://doi.org/10.1007/s11243-015-9958-6

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