Electron-Transfer Properties of the Phenolate Anion Derived from a Vitamin E Model in the Presence of a Strong Base in an Aprotic Medium

The phenolate anion derived from a vitamin E model, 2,2,5,7,8-pentamethylchroman-6-ol (PMC), in the presence of a strong base is reported to reduce molecular oxygen to generate superoxide anion, one of reactive oxygen species, in acetonitrile (MeCN) (Org. Biomol. Chem. 1:4085; 2003). However, very little is known about the detailed electron-transfer properties of phenolate anions derived from phenolic antioxidants. In this study, we report the PMC anion can act as a strong electron donor to 2,2-diphenyl-1-picrylhydrazyl radical as well as to a series of p-benzoquinones in MeCN. The kinetic data obtained in this study were evaluated in light of the Marcus theory of electron transfer, providing valuable insight into the electron-transfer properties of the phenolate anions derived from phenolic antioxidants.SFRBM/SFRRI 201