Get access

Isatin-Schiff base copper(II) complexes—A DFT study of the metal-ligand bonding situation

Authors

  • Giovanni F. Caramori,

    Corresponding author
    1. Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, P.O. Box 26077, CEP 05513-970, São Paulo, SP, Brazil
    2. Departamento de Química, CFM, Universidade Federal de Santa Catarina, UFSC, Campus Universitário Trindade, C.P. 476, 88040-900, Florianópolis, SC, Brazil
    • Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, P.O. Box 26077, CEP 05513-970, São Paulo, SP, Brazil
    Search for more papers by this author
  • Renato L. T. Parreira,

    1. Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Av. Bandeirantes 3900, 14040-901, Ribeirão Preto, SP, Brazil
    Search for more papers by this author
  • Ana Maria Da Costa Ferreira

    1. Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, P.O. Box 26077, CEP 05513-970, São Paulo, SP, Brazil
    Search for more papers by this author

Abstract

Herein, we report results of calculations based on density functional theory (BP86/TZVP) of a set of isatin-Schiff base copper(II) and related complexes, 1-12, that have shown significant pro-apoptotic activity toward diverse tumor cells. The interaction of the copper(II) cation with different ligands has been investigated at the same level of theory. The strength and character of the Cu(II)-L bonding was characterized by metal-ligand bond lengths, vibrational frequencies, binding energies, ligand deformation energies, and natural population analysis. The metal-ligand bonding situation was also characterized by using two complementary topological approaches, the quantum theory of atoms-in-molecules (QTAIM) and the electron localization function (ELF). The calculated electronic g-tensor and hyperfine coupling constants present significant agreement with the EPR experimental data. The calculated parameters pointed to complex 10 as the most stable among the isatin-Schiff base copper(II) species, in good agreement with experimental data that indicate this complex as the most reactive in the series. © 2011 Wiley Periodicals, Inc. Int J Quantum Chem, 2012

Ancillary