Correlation analysis in the reactions of benzyl bromide with N-substituted anilines

Abstract

The nucleophilic substitution reaction between benzyl bromide and N-substituted anilines in methanol medium suggests that the reactivity of the nucleophiles increases with their pkb values. A linear relationship exists between the rate and the computed values of the dipole moment and electronegativity of the nucleophiles. The frontier orbital interactions and correlation of rate with HOMO-LUMO gap of the two reactants suggest that the reaction is not orbital controlled but is controlled by the electrostatic interactions between the reactants.