TY - JOUR
T1 - Homolytic and heterolytic O-H bond cleavage in trans-resveratrol and some phenantrene analogs
T2 - A theoretical study
AU - Benayahoum, Ali
AU - Amira-Guebailia, Habiba
AU - Houache, Omar
PY - 2014/6/1
Y1 - 2014/6/1
N2 - 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.
AB - 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.
KW - DFT
KW - ETE and SPLET
KW - HAT AIP
KW - PA
KW - Phenanthrene
KW - Resveratrol
UR - http://www.scopus.com/inward/record.url?scp=84897952345&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84897952345&partnerID=8YFLogxK
U2 - 10.1016/j.comptc.2014.03.016
DO - 10.1016/j.comptc.2014.03.016
M3 - Article
AN - SCOPUS:84897952345
SN - 2210-271X
VL - 1037
SP - 1
EP - 9
JO - Computational and Theoretical Chemistry
JF - Computational and Theoretical Chemistry
ER -