Kinetic data is an elegant tool to quantitatively assess structure-reactivity correlation of organic substrates in reactions and is immaculate if endorsed with complementary information. Halogenations of aromatic substrates in aqueous medium are rapid reactions necessitating special techniques for their study. Their rates depend on nature of the reagents, nucleophilicity of the substrates, and steric compulsions involved. Herein, the rapid uncatalyzed chlorination kinetics of six regioisomers of xylenol by aqueous chlorine has been investigated using hydrodynamic voltammetry. These data have been supported with those obtained from molecular docking studies of the xylenol regioisomers with acetylcholinesterase in this two-pronged approach. The magnitudes of the velocity constants, energies of activation, frequency factors, and entropy of activation in these six reactions assess, quantitatively and unambiguously, the reactivity of the regioisomers of xylenol when complemented with the binding energy data obtained from molecular docking.