Abstract

AbstractThe rates of base‐catalyzed hydrogen‐deuterium exchange at C‐2 in some 6‐substituted benzothiazoles were studied and compared with the analogous values pertinent to some 5‐substituted benzothiazoles, reported in a previous paper. The simple Hammett equation was found not to allow a good interpretation of the experimental data. However, a good agreement was obtained by the application of the Hammett‐Jaffé equations. From these calculations, it was concluded that the sulphur and the nitrogen heteroatoms of the thiazole ring have, in these reactions, a very similar activity in the transmission of the substituent effects from the benzo ring at C‐2 of the thiazole ring. Therefore, while in other reactions only the nitrogen heteroatom is active, in these reactions a considerable stabilization of the α‐carbanion is clearly shown also by the sulphur heteroatom.

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