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Acta Chimica Slovaca

The Journal of Slovak University of Technology in Bratislava

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1337-978X
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Acidic and alkaline bimolecular hydrolysis of substituted formanilides. Computational analysis and modelling of substitution effects

Martin Michalík
  • Corresponding author
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
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/ Peter Škorňa
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Vladimír Lukeš
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
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  • De Gruyter OnlineGoogle Scholar
/ Erik Klein
  • Institute of Physical Chemistry and Chemical Physics, Slovak University of Technology in Bratislava, Radlinského 9, SK-812 37 Bratislava, Slovakia
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Published Online: 2017-06-23 | DOI: https://doi.org/10.1515/acs-2017-0006

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.

Keywords: Substituent Effect; Chemical Kinetics; Model Compound; Thermodynamic; Trans Isomer; Cis Isomer

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About the article

Published Online: 2017-06-23

Published in Print: 2017-04-25


Citation Information: Acta Chimica Slovaca, ISSN (Online) 1337-978X, DOI: https://doi.org/10.1515/acs-2017-0006.

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© Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava . This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License. BY-NC-ND 4.0

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