Acidic and alkaline bimolecular hydrolysis of substituted formanilides. Computational analysis and modelling of substitution effects

Author:

Michalík Martin1,Škorňa Peter1,Lukeš Vladimír1,Klein Erik1

Affiliation:

1. Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava , Slovakia

Abstract

Abstract In this article, the study of 67 compounds representing various para-, meta- and ortho- substituted formanilides is presented. These molecules and the products of their acidic and alkaline hydrolysis were studied using DFT quantum chemical methods in order to calculate the reaction enthalpies. These enthalpies are correlated with the hydrolysis rate constants, kH, published for the acid-catalysed acyl cleavage bimolecular (AAC2) mechanism and the modified base-catalysed acyl cleavage bimolecular (BAC2) mechanism. The found linear dependences can be used for the prediction of rate constants of non-synthesised formanilide derivatives.

Publisher

Walter de Gruyter GmbH

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