N-Chlorination of secondary amides. I. Kinetics of N-chlorination of N-methyl acetamide

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Abstract
The rate of N-chlorination of N-methyl acetamide has been studied in acetate buffered hypochlorous acid solutions. The reaction rate is dependent upon pH, chloride ion concentration, and acetic acid concentration. The results fit the following rate expression[Formula: see text]The observed rate constant, kobs, has three components[Formula: see text]The results suggest that the active chlorinating species in the pH range 3.0–6.0 are HOCl, Cl2, and CH3COOCl, in order of increasing reactivity. The values of the corresponding rate constants at 25 °C are [Formula: see text], and [Formula: see text] l mole−1 min−1, the last two rate constants being related to k2 and k3 through the respective equilibrium constants.At temperatures near room temperature, the N-chlorination reaction has an apparent activation energy of 14 kcal/mole when Cl2 is the active species, and 5 kcal/mole when CH3COOCl is the chlorinating agent.

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