Preprint Article Version 2 Preserved in Portico This version is not peer-reviewed

Theoretical DFT Study of the Antioxidant Activity of Five Plant Food Benzoic Acid Derivatives: Dearomatization and Stability of H Abstraction Radicals

Bienfait Kabuyaya Isamura
* ORCID logo ,
Issofa Patouossa
,
Isaac Kaba Elaka
,
Aristote Matondo
,
Pius Tshimankinda Mpiana
*
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. Theoretical DFT Study of the Antioxidant Activity of Five Plant Food Benzoic Acid Derivatives: Dearomatization and Stability of H Abstraction Radicals. Preprints 2022, 2022010095. https://doi.org/10.20944/preprints202201.0095.v2 Isamura, B.K.; Patouossa, I.; Elaka, I.K.; Matondo, A.; Mpiana, P.T. Theoretical DFT Study of the Antioxidant Activity of Five Plant Food Benzoic Acid Derivatives: Dearomatization and Stability of H Abstraction Radicals. Preprints 2022, 2022010095. https://doi.org/10.20944/preprints202201.0095.v2

Abstract

This study reports a computational investigation on the antioxidant activity of five plant food benzoic acid derivatives, namely gallic acid (GA), para-hydroxybenzoic acid (PHBA), protocatechuic acid (PCA), syringic acid (SA), and vanillic acid (VA). Based on computed thermodynamics parameters, a detailed comparative debate is developed concerning their free radical scavenging activity in the gas phase and polar solutions (in water and methanol solvents). This discussion goes on to elucidate both the most preferred mechanism and the order of antioxidant activity for these molecules in each environment. Paradoxically, calculations using the harmonic oscillator model of aromaticity (HOMA) suggest that H abstraction radicals gain in stability as the central benzene ring loses in structural aromaticity. Finally, spin densities and fukui function f0 seem to be good indicators of the local reactivity of these compounds towards free radicals.

Keywords

antioxidant activity; eearomatization; frontier molecular orbital; fukui function f0; DFT

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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Comments (1)

Comment 1
Received: 3 February 2022
Commenter: Bienfait Kabuyaya Isamura
Commenter's Conflict of Interests: Author
Comment: The paper has been revised as follows:
1. The stability of H abstraction radicals has been discussed in terms of structural aromaticity
2. Fukui function f0 have been computed to predict local reactivity of the five benzoic acid derivatives towards free radicals
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