Kinetics and mechanism of dehydrochlorination of N-aryl-C-ethoxycarbonylformohydrazidoyl chlorides

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Abstract

The kinetics of triethylamine (TEA) catalyzed deydrochlorination of a series of N-aryl-C-ethoxycarbonylformohydrazidoyl chlorides 1a–m have been studied under pseudo-first-order conditions in 4:1 (v/v) dioxane–water solution at 30 °C. For all compounds studied, the kinetics followed the rate law: k obs = k 2 (TEA). The values of the overall second-order rate constants for the studied compounds were correlated by the equation: log k 2 = 0.533σ − -0.218. The results are compatible with a mechanism involving a fast reversible deprotonation step leading to the anion of 1, followed by rate-determining step involving the loss of the chloride ion from the anion. The reaction constants of these two steps were estimated to be 0.845 and −0.312, respectively.

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