<abstract xmlns="http://www.w3.org/1999/xhtml"><p>The DFT study of primary antioxidant action of gallic acid and its carboxylic anion is presented in the gas-phase, benzene and water. Corresponding reaction enthalpies for three possible mechanisms was calculated using B3LYP/6-311++G** method. Bond dissociation enthalpy (BDE) and proton dissociation enthalpy (PDE) of 4-OH group was found to be the lowest in gas-phase as well as in both solvents approximated by IEF-PCM model. Ionization potentials (IPs) were higher than BDEs in all cases. Deprotonation of carboxylic group result in increased antioxidant potency as drop in BDE, proton affinities (PAs) and IPs was indicated in all environments.</p></abstract>

The DFT study of primary antioxidant action of gallic acid and its carboxylic anion is presented in the gas-phase, benzene and water. Corresponding reaction enthalpies for three possible mechanisms was calculated using B3LYP/6-311++G** method. Bond dissociation enthalpy (BDE) and proton dissociation enthalpy (PDE) of 4-OH group was found to be the lowest in gas-phase as well as in both solvents approximated by IEF-PCM model. Ionization potentials (IPs) were higher than BDEs in all cases. Deprotonation of carboxylic group result in increased antioxidant potency as drop in BDE, proton affinities (PAs) and IPs was indicated in all environments.

Gallic acid: thermodynamics of the homolytic and heterolytic phenolic O—H bonds splitting-off

Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava,

Acta Chimica Slovaca

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

The DFT study of primary antioxidant action of gallic acid and its carboxylic anion is presented in the gas-phase, benzene and water. Corresponding reaction...

Gallic acid: thermodynamics of the homolytic and heterolytic phenolic O—H bonds splitting-off

Published Online: Dec 08, 2016

Page range: 114 - 123

DOI: https://doi.org/10.1515/acs-2016-0020

Keywords
hydrogen atom transfer, sequential proton-loss electron-transfer, deprotonation, bond dissociation enthalpy, proton affinity

© 2016 Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Gallic acid: thermodynamics of the homolytic and heterolytic phenolic O—H bonds splitting-off

Published Online: Dec 08, 2016

Page range: 114 - 123

DOI: https://doi.org/10.1515/acs-2016-0020

Keywordshydrogen atom transfer, sequential proton-loss electron-transfer, deprotonation, bond dissociation enthalpy, proton affinity

© 2016 Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

Keywords
hydrogen atom transfer, sequential proton-loss electron-transfer, deprotonation, bond dissociation enthalpy, proton affinity