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Journal of Chemistry
Volume 2017, Article ID 5936239, 9 pages
https://doi.org/10.1155/2017/5936239
Research Article

Free Radical Scavenging Potency of Dihydroxybenzoic Acids

1Bioengineering Research and Development Center, 34000 Kragujevac, Serbia
2Department of Chemical-Technological Sciences, State University of Novi Pazar, Vuka Karadžića bb, 36300 Novi Pazar, Serbia
3Faculty of Physical Chemistry, University of Belgrade, Studentski trg 12-16, 11000 Belgrade, Serbia

Correspondence should be addressed to Dejan Milenković; sr.ca.gk@28iked

Received 2 January 2017; Accepted 9 February 2017; Published 26 February 2017

Academic Editor: Yuan-Pern Lee

Copyright © 2017 Dejan Milenković et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

In order to evaluate the free radical scavenging potency of dihydroxybenzoic acids (DHBAs) the Density Functional Theory (DFT) was used. The M05-2X/6-311++G(d,p) and B3LYP-D2/6-311++G(d,p) theoretical models were applied. Three possible antioxidant mechanisms were examined: hydrogen atom transfer (HAT), single-electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) mechanisms. All of these mechanisms have been studied in nonpolar (benzene and pentylethanoate) and polar solvents (water) using an implicit solvation model (SMD). The following thermodynamic quantities related to these mechanisms were calculated: bond dissociation enthalpy (BDE), ionization potential (IP), and proton affinity (PA). The obtained results indicated the HAT mechanism as the most favourable reaction pathway for antioxidative action of DHBAs in benzene. On the other hand, SPLET is indicated as predominant reaction mechanism in polar solvent. The SET-PT mechanism was not favourable reaction path for antioxidative action in any of the solvents under investigation.