Kinetics of aromatic nucleophilic substitution reactions of 2-chloroquinoxaline with anilines

Abstract

Rate constants for the reactions of 2-chloroquinoxaline with various aniline derivatives in methanol have been measured at four different temperatures. The reactions are accelerated by electron- releasing, and retarded by electron-withdrawing, substituents on aniline. A second-order kinetics, first order with respect to both substrate and reagent is observed with all the anilines. The rate data are correlated with both Hammett and Bronsted relations. The activation parameters supported SN2Ar mechanism.