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Effects of Nonionic Micelles on the Rate of Mononuclear Heterocyclic Rearrangement of (Z)-Phenylhydrazones of 5-Substituted 3-Benzoyl-1,2,4-oxadiazoles

✍ Scribed by Susanna Guernelli; Renato Noto; Carmelo Sbriziolo; Domenico Spinelli; Maria Liria Turco Liveri

Publisher: Elsevier Science
Year: 2001
Tongue: English
Weight: 65 KB
Volume: 239
Category: Article
ISSN: 0021-9797
DOI: 10.1006/jcis.2001.7558

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✦ Synopsis

Nonionic Triton X-100 micelles solubilize the otherwise waterinsoluble (Z)-phenylhydrazones of some 5-substituted 3-benzoyl-1,2,4-oxadiazoles to an extent suitable for studying the occurrence of a general-base-catalyzed rearrangement in the presence of borate buffers (pH 9.6). The kinetic data, obtained at 40.0 • C over a wide range of surfactant concentrations, are found to conform to a reaction scheme which implies partitioning of the substrates and the base between water and the micellar pseudophase. Evidence that both the rate of the rearrangement reactions and the binding of the substrates to the micellar aggregates are primarily governed by the steric requirements of the 5-substituent group is obtained.

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