Oxidation of paracetamol (PAM) by sodium N-chlorobenzenesulphonamide (chloramine-B or CAB) in HClO4 medium at 30°C was studied. The rate is first order in [CAB]0 and fractional order each in [PAM]0 and [H+]. Variation of ionic strength and addition of the reaction product benzenesulphonamide or halide ions had no significant effect on the reaction rate. The solvent isotope effect was studied using D2O. Decrease in dielectric constant of the medium increases the rate. Activation parameters for the overall reaction have been computed. Michaelis-Menten type of kinetics has been proposed and activation parameters for the rate-limiting step have also been computed. 4-Amino-2,6-dichlorophenol was identified as the oxidation product of PAM. A mechanism consistent with the observed results is proposed and discussed.
Volume 132, 2019
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