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.
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