Density Functional Theory (B3LYP) Study of Substituent Effects on O?H Bond Dissociation Enthalpies of trans-Resveratrol Derivatives and the Role of Intramolecular Hydrogen Bonds

摘要

In this paper, 23 substituents with variousnelectron-donating and electron-withdrawing characters werenplaced in available positions of trans-resveratrol in order tonstudy their effect on the three O−H bond dissociationnenthalpies (BDEs) via density functional theory (DFT) withnBecke three-parameter exchange and Lee−Yang−Parr correlationn(B3LYP). It has been found that the mutual positions ofnsubstituents and OH groups affect investigated BDEs substantially.nFormation of strong intramolecular hydrogen bondsnand suitable spin density distributions in several radicals result innlow BDEs. Calculated BDEs have been correlated withnHammett constants, selected geometry parameters, and chargenon phenoxy radical oxygen q(O). Found dependences arensatisfactorily linear.