Abstract
The oxidation rate of 4-acetamidophenol or paracetamol (PAM) by bromamine-T (BAT) in HClO4 solutions at 303 K shows a first-order dependence on [BAT] and a fractional-order dependence each on [PAM] and [H+]. The variation of ionic strength of the medium and addition of the reduction product of BAT and halide ions have no significant effect on the rate. The solvent dielectric constant shows a positive effect on the rate. A solvent isotope effect of k′(H2O)/k′(D2O) = 0.88 has been observed. The reaction mixture fails to induce polymerization of acrylonitrile suggesting the absence of in situ free-radical formation. Michaelis-Menten type of kinetics has been proposed and activation parameters for the rate-determining step and for the composite reaction have been determined. Formation and decomposition constants have been evaluated. The protonated oxidant, ArNH2Br+, is assumed to be the reactive species. The oxidation product of PAM has been characterized as 4-amino-2,6-dibromophenol. A plausible mechanism consistent with the kinetic data has been proposed.
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