Effects of Molecular Association on the Rates of Hydrolysis of Long-Chain Alkyl Betainates (Alkoxycarbonyl-N,N,N-Trialkylmethanaminium Halides).

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Abstract
Alkaline hydrolysis of long-chain alkyl betainates (alkoxycarbonyl-N,N,N-trialkylmethanaminium halides) is accelerated by molecular aggregation leading to micellization. With increasing length of the alkyl chain, the observed rate constant shows an increased concentration dependence and an increased deviation from pseudo first-order kinetics at constant pH. The rate constant reached a maximum at an ester concentration close to the estimated critical micelle concentration. Thus, at a ca. 400 .mu.M ester concentration the C14 compound was hydrolyzed roughly ten times faster than its C3 analogue, while extrapolation to zero concentration gave virtually identical rate constants. The results are best interpreted by means of the pseudophase ion-exchange model.

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