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

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.