Flavonoids are a big class of natural product and have a wide range of biological activities. Some of these applications depend on its antioxidant capacity. Nevertheless, another mechanism can be involved by means of alkylation reaction on α,β-unsaturated carbonyl system. This study aimed to evaluate the antioxidant capacity and the chemical reactivity among simplified flavonoid derivatives and isoxazolone analogous as Michael system by using B3LYP functional and 6-311 g(d,p) basis set. Frontier molecular orbital, ionization potential (IP), spin density contributions, and Fukui index explain the antioxidant capacity and reactivity index on isoxazolone and its related derivatives. The best contribution at β-alkene moiety is related to better reactivity of α,β-unsaturated carbonyl group. A decrease in antioxidant capacity is related to an increase in the chemical reactivity index. The frontier molecular orbitals show that aurone is more reactive than isoxazolone. In accordance with Fukui index, isoxazolone can be better inhibitor as Michael system when compared to flavonoid derivatives. Graphical abstract.
Keywords: Antioxidant; DFT; Flavonoids derivatives; Isoxazolone; Reactivity.