Abstract
Kinetic studies by stopped-flow spectrophotometry are reported for the reactions of 1,3,5-trinitrobenzene with n-butylamine, benzylamine, isopropylamine, or piperidine in dimethyl sulphoxide. These reactions lead to the formation of anionic σ-adducts via zwitterionic intermediates and it is shown that proton-transfer may be kinetically significant. Reduction below the values expected for diffusion-control in the values of rate constants for proton-transfer between the zwitterions and amines is attributed to a steric effects which is more pronounced in the reaction involving piperidine than in the reactions of primary amines.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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