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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Substituent Effects on the Micelle-Catalysed and Uncatalysed Basic Hydrolysis of a Series of Substituted N-Methyl-p-toluanilides

TJ Broxton and NW Duddy

Australian Journal of Chemistry 32(8) 1717 - 1726
Published: 1979

Abstract

The rate of hydrolysis of a series of substituted N-methyl-p-toluanilides has been measured in water and in the presence of cationic micelles [cetyltrimethylammonium bromide (ctab)]. A Hammett correlation of the rates of hydrolysis gave a curved Hammett plot for the reaction in water (k2,W) but a linear plot for the rate of reaction at optimal concentrations of ctab (k2,max) and for derived rate constants within the micelle (k2,m) These results are discussed in terms of the mechanism of reaction, and for two compounds a micelle-induced change of mechanism is indicated.

https://doi.org/10.1071/CH9791717

© CSIRO 1979

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