A quantitative assessment of the reactivity of the regioisomers of xylenol by investigation of rapid chlorination kinetics in aqueous solution employing hydrodynamic voltammetry complemented by molecular docking with acetylcholinesterase: A two‐pronged approach

Abstract

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.

A novel ternary approach to quantitatively assess the reactivity of nitroaniline regioisomers by investigation of rapid iodination kinetics using hydrodynamic voltammetry, reduction propensities from polarography, and binding affinities from molecular docking simulations

“…Recently, the applicability of the Hammett equation from such studies of iodination of phenols in aqueous medium has been manifested 4 . More recently, a quantitative assessment of the reactivity of xylenol regioisomers has been carried out on the basis of kinetic proofs complemented with molecular docking studies 5 . Herein, the quantitative structure–reactivity assessment studies of the three regioisomers of nitroaniline—2‐nitroaniline (2‐NA), 3‐nitroaniline (3‐NA), and 4‐nitroaniline (4‐NA)—have been investigated on the basis of three realms—kinetic evidence, polarographic studies, and molecular docking simulations.…”