The reactivity of N-phenylanthranilic acids derivatives. XXV. Kinetic parameters of activation and isoparametricity of the reaction of the alkaline hydrolysis of methyl esters of substituted 4,5-dimethoxy-N-phenylanthranilic acids in the binary dioxane-water solvent

Authors

  • S. G. Isaev National University of Pharmacy, Ukraine
  • O. M. Sviechnikova National Kharkiv Pedagogical University named after G.S. Skovoroda, Ukraine
  • A. O. Devyatkina National University of Pharmacy, Ukraine
  • T. A. Kostina National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.779

Keywords:

N-phenylanthranilic acid, methyl esters, reactivity, thermodynamic parameters of activation, isoparametricity of reactions, enthalpy control

Abstract

Kinetics of the alkaline hydrolysis reaction of methyl esters of substituted 4,5-dimethoxy-N-phenylanthranilic acids has been studied in the binary solvent of dioxane-water at 55, 75, 85°C. It has been found that at each experimental temperatures lgkT dependence on the nature and position of substitutes in a non-anthranilic fragment of the molecule is described by the Hammett equation. It has been demonstrated that introduction of electrodonor substituents in the molecule of ester assists increasing of the activation energy and free activation energy. The activation entropy for all substances is significant and high according to the absolute value, which indicates the BAC2 mechanism of the reaction with formation of high-symmetrical intermediates. The analysis of the numerous kinetic and activation parameters has shown isokinetics of the reaction with the enthalpy type of control. It has been experimentally found that the compounds synthesized show the anti-inflammatory, analgesic, diuretic, bacteriostatic activities.

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Published

2014-03-06

How to Cite

(1)
Isaev, S. G.; Sviechnikova, O. M.; Devyatkina, A. O.; Kostina, T. A. The Reactivity of N-Phenylanthranilic Acids Derivatives. XXV. Kinetic Parameters of Activation and Isoparametricity of the Reaction of the Alkaline Hydrolysis of Methyl Esters of Substituted 4,5-Dimethoxy-N-Phenylanthranilic Acids in the Binary Dioxane-Water Solvent. J. Org. Pharm. Chem. 2014, 12, 69-73.

Issue

Vol. 12 No. 1(45) (2014)

Section

Original Researches

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