Homolytic and heterolytic O-H bond cleavage in trans-resveratrol and some phenantrene analogs: A theoretical study

Ali Benayahoum, Habiba Amira-Guebailia, Omar Houache

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

In this article, quantum chemical calculations based on the density functional theory (DFT) have been used to study the relationship between the structure and the antioxidant activity of trans-resveratrol (RSV) and its phenantrene analogs in the gas phase, benzene and water. Our investigation includes H-atom transfer (HAT), single electron transfer-proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) mechanisms. The calculated values were in good agreement with the experimental results. Like other phenolic compounds, the H-atom transfer mechanism is the thermodynamically preferred mechanism in vacuum, for the studied molecules. While, the SPLET mechanism is the thermodynamically favorable pathway in water. Our calculations suggest that, SET-PT is not the most preferred mechanism in all environments studied.

Original languageEnglish
Pages (from-to)1-9
Number of pages9
JournalComputational and Theoretical Chemistry
Volume1037
DOIs
Publication statusPublished - Jun 1 2014

Fingerprint

Protons
cleavage
Theoretical Models
Electrons
analogs
electron transfer
Proton transfer
protons
Atoms
Water
Vacuum
Benzene
Density functional theory
antioxidants
Antioxidants
Gases
water
atoms
Hydrogen
Molecules

Keywords

  • DFT
  • ETE and SPLET
  • HAT AIP
  • PA
  • Phenanthrene
  • Resveratrol

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Biochemistry
  • Condensed Matter Physics

Cite this

Homolytic and heterolytic O-H bond cleavage in trans-resveratrol and some phenantrene analogs : A theoretical study. / Benayahoum, Ali; Amira-Guebailia, Habiba; Houache, Omar.

In: Computational and Theoretical Chemistry, Vol. 1037, 01.06.2014, p. 1-9.

Research output: Contribution to journalArticle

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