Version 1
: Received: 29 December 2021 / Approved: 6 January 2022 / Online: 6 January 2022 (18:04:32 CET)
Version 2
: Received: 31 January 2022 / Approved: 3 February 2022 / Online: 3 February 2022 (15:19:51 CET)
How to cite:
Isamura, B.K.; Patouossa, I.; Elaka, I.K.; Matondo, A.; Mpiana, P.T. Free Radical Scavenging Activity of Five Benzoic Acid Derivatives: A Theoretical M06-2X Study. Preprints2022, 2022010095. https://doi.org/10.20944/preprints202201.0095.v1
Isamura, B.K.; Patouossa, I.; Elaka, I.K.; Matondo, A.; Mpiana, P.T. Free Radical Scavenging Activity of Five Benzoic Acid Derivatives: A Theoretical M06-2X Study. Preprints 2022, 2022010095. https://doi.org/10.20944/preprints202201.0095.v1
Isamura, B.K.; Patouossa, I.; Elaka, I.K.; Matondo, A.; Mpiana, P.T. Free Radical Scavenging Activity of Five Benzoic Acid Derivatives: A Theoretical M06-2X Study. Preprints2022, 2022010095. https://doi.org/10.20944/preprints202201.0095.v1
APA Style
Isamura, B.K., Patouossa, I., Elaka, I.K., Matondo, A., & Mpiana, P.T. (2022). Free Radical Scavenging Activity of Five Benzoic Acid Derivatives: A Theoretical M06-2X Study. Preprints. https://doi.org/10.20944/preprints202201.0095.v1
Chicago/Turabian Style
Isamura, B.K., Aristote Matondo and Pius Tshimankinda Mpiana. 2022 "Free Radical Scavenging Activity of Five Benzoic Acid Derivatives: A Theoretical M06-2X Study" Preprints. https://doi.org/10.20944/preprints202201.0095.v1
Abstract
The meta hybrid M06-2X functional combined with the 6-311++G(d,p) basis set are used to investigate the antioxidant activity of five benzoic acid derivatives naturally occurring in several plant food: gallic acid, para-hydroxybenzoic acid, protocatechuic acid, syringic acid and vanillic acid. To assess the antioxidant properties of these compounds, three mechanisms of free radicals scavenging are considered, namely the hydrogen atom transfer (HAT), stepwise electron transfer proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) models. The effect of polar environments on the antioxidant power of these compounds is mimicked in water and methanol using the IEF-PCM solvation method. Our findings suggest that HAT is the preferred mechanistic pathway in gas phase, while SPLET is favoured in polar mediums. Protocatechuic and gallic acids are the most active in gas and polar solutions respectively, whereas PHBA is the least active in all the environments considered. The O-H group in para position of the carboxylic group (O3-H for GA and O2-H for the rest) is confirmed to be the most reactive site in gas phase, while in solution it is either of the O1-H site (for PHBA, PCA, SA and VA) or O4-H groups (for GA). The “HOMO-rule” of free radical scavenging ability does not seem to account properly for the antioxidant properties of this set of chemicals.
Keywords
Antioxidant activity, HAT, SET-PT, SPLET, frontier molecular orbital
Subject
Chemistry and Materials Science, Theoretical Chemistry
Copyright:
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.
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