Density functional theory calculations for resveratrol

The calculations based on the density functional theory (DFT) have been used to study the structure–activity of resveratrol in the chain reaction of autooxidation. According to the geometry obtained by using a B3LYP/6-31G**, the HOMO, LUMO of resveratrol and the spin density, the single electron distribution of the 4′- and 5-radical of resveratrol were calculated, it was found that resveratrol is a potential antioxidant. The 4′-hydroxyl group of resveratrol is more reactive than 3- and 5-positions because of the resonance effects. The dominant structure of the resveratrol radicals is a semiquinone structure which determines the stability of radicals, and the unpaired electron is mainly distributed to the O-atom and its ortho and para positions. The antioxidant activity of resveratrol is related to the spin density and the unpaired electron distribution of the O-atom. [Copyright &y& Elsevier]