Effect of the Environment on the Reactivity of 4′-Substituted Flavones and Isoflavones

The reactivity of flavones and isoflavones, substituted at the 4′ position by several types of electron-withdrawing or electron-donating groups, was studied by FMO theory in the gas-phase and in aqueous solution. The predictions of this theory were consistent with the experimental reactivity of analogue compounds, and also with the stability of the products of reaction of these compounds with different nucleophilic and electrophilic reagents. The preferences found in the gas-phase for the sites of reaction are retained in aqueous solution.