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Deprotonation of flavonoids severely alters the thermodynamics of the hydrogen atom transfer

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    0472529 - ÚFCH JH 2017 RIV NL eng J - Článek v odborném periodiku
    Klein, E. - Rimarčík, J. - Senajová, E. - Vagánek, A. - Lengyel, Jozef
    Deprotonation of flavonoids severely alters the thermodynamics of the hydrogen atom transfer.
    Computational and Theoretical Chemistry. Roč. 1085, JUN 2016 (2016), s. 7-17. ISSN 2210-271X. E-ISSN 1872-7999
    Grant CEP: GA ČR GA14-14082S
    Institucionální podpora: RVO:61388955
    Klíčová slova: Primary antioxidant * Flavonoid * dft * Bond dissociation enthalpy * Sequential proton-loss electron-transfer
    Kód oboru RIV: CF - Fyzikální chemie a teoretická chemie
    Impakt faktor: 1.549, rok: 2016

    Deprotonated polyphenolics exhibit different free radical scavenging activity than parent molecules. Therefore, this study is focused on the hydrogen atom transfer (HAT) from mono-deprotonated forms (phenoxide anions) of 16 flavonoids in terms of O-H bond dissociation enthalpies, BDE(A), using B3LYP/6-311++G** approach. Solvent (benzene and water) contribution is computed using integral equation formalism polarized continuum model, IEF-PCM. Obtained BDE(A) values are usually lower than BDEs of the parent species. In general, from the thermodynamic point of view, HAT from a phenoxide anion is favored to the electron transfer, i.e. formation of the phenoxy radical. For the studied environments, preferred radical anions are identified. Obtained results can contribute to the explanation of experimentally observed pH dependent antioxidant effect of polyphenolics. (C) 2016 Elsevier B.V. All rights reserved.
    Trvalý link: http://hdl.handle.net/11104/0269822

     
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