Kinetic Study of Chlorination of P-Methoxyacetanilide by Chloramine-T in Hydrochloric Acid Medium

The kinetics of chlorination of p-methoxyacetanilide by sodium N-chloro-p-toulenesulphonamide, chloramine-T (CAT) in the presence of HCl has been investigated at 30 °C. The reaction shows first-order dependence each on (CAT) and [H+] and is independent on [substrate]. The variation of the ionic strength of the medium has no significant effect on the reaction rate, Addition of the reaction product (p.toluenesulphonamide) retards the rate while addition of chloride ion or an increase in the ethanol proportion (decrease he dielectric constant of the medium) accelerate the reaction rate. The chlorination process under condition employed in the present investigation has been shown to proceed via either the interaction of p.methoxy acetanilide with H2O+Cl or HOCl with protonated p-methoxy acetanilide to give the product. Finally, the activation parameters for the reaction were also calculated.