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Use of PM6 quantum-chemical calculations in studying the properties of antioxidants in the biological environment

  • Chemical Physics of Biological Processes
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Abstract

The energies of formation, enthalpies, and entropies of the conformers of 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionic acid and sodium and potassium 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionates are calculated by quantum-chemical methods in the PM6 approximation. A doubling of signals in the 1H NMR spectrum of the first conformer is observed, which merge into singlets when the compound is heated. Changes in the structure of the conformers and donor-acceptor complexes (solvates) occur with the preservation of the metal-ligand coordination bond. Calculations of the characteristics of 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionic acid and sodium and potassium 1-(carboxy)-1-(N-methylamide)-2-(3′,5′-di-tert-butyl)-4-hydroxyphenyl)-propionates in the PM6 approximation make it possible to predict the structure and properties of the solvated structures. The energies of homolysis of the H-O bond D (OH) are calculated, and a linear dependence of the antioxidant activity on D (OH) for the structures of the studied compounds is demonstrated. The results make it possible to predict the properties of antioxidants in the biological environment.

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Authors and Affiliations

  1. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Moscow, Russia

    A. A. Volod’kin, G. E. Zaikov, L. N. Kurkovskaya & E. B. Burlakova

Authors
  1. A. A. Volod’kin
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  2. G. E. Zaikov
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  3. L. N. Kurkovskaya
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  4. E. B. Burlakova
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Correspondence to A. A. Volod’kin.

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Original Russian Text © A.A. Volod’kin, G.E. Zaikov, L.N. Kurkovskaya, E.B. Burlakova, 2011, published in Khimicheskaya Fizika, 2011, Vol. 30, No. 10, pp. 72–81.

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Volod’kin, A.A., Zaikov, G.E., Kurkovskaya, L.N. et al. Use of PM6 quantum-chemical calculations in studying the properties of antioxidants in the biological environment. Russ. J. Phys. Chem. B 5, 836–845 (2011). https://doi.org/10.1134/S1990793111090235

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  • DOI: https://doi.org/10.1134/S1990793111090235

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