Predicting the activity of methoxyphenol derivatives antioxidants: II—Importance of the nature of the solvent on the mechanism, a DFT study

Abstract

AbstractThe various mechanisms of primary antioxidant action of a series of 2‐Methoxyphenols are investigated in the present work. The electronic properties have just been studied in a joint article, so that we focus here on Hydrogen Atom Transfer (HAT), Single Electron Transfer–Proton Transfer (SET–PT) and Sequential Proton‐Loss Electron‐Transfer (SPLET) mechanisms. The two computational approaches used in the previous study of the structure and reactivity of these compounds [Computational and Theoretical Chemistry 1229 (2023) 114287] provide identical mechanisms trends in gas phase. In gas media, hydrogen atom transfer (HAT) is more favored. On the contrary, the solvent polarity has a significant effect on the mechanism of the antioxidant activity, since the polarity of the solvent increases the contribution of the SPLET mechanism.