Thermodynamics of the Hydrolysis Reactions of Nitriles

Published

July 1, 2005

Author(s)

Yadu D. Tewari, Robert N. Goldberg

Abstract

Microcalorimetry and high-performance liquid chromatography (h.p.l.c) have been used to conduct a thermodynamic investigation of the following nitrilase catalyzed reactions: (1) benzonitrile(aq) + 2 H2O(l) = benzoic acid(aq) + ammonia(aq), (2) benzylcyanide(aq) + 2 H2O(l) = benzeneacetic acid(aq) + ammonia(aq), (3) 3-phenylpropionitrile(aq) + 2 H2O(l) = 3-phenylpropanoic acid(aq) + ammonia(aq), (4) 4?phenylbutyonitrile(aq) + 2 H2O(l) = 4-phenylbutyric acid(aq) + ammonia(aq), (5) a-methylbenzyl-cyanide(aq) + 2 H2O(l) = a-methylbenzene acetic acid(aq) + ammonia(aq), and (6) 3?indoleacetonitrile(aq) + 2 H2O(l) = indole-3-acetic acid(aq) + ammonia(aq). The equilibrium measurements showed that these reactions proceeded to completion. Thus, it was possible to set only lower limits for the values of the apparent equilibrium constants K . However, it was possible to obtain precise values of the calorimetrically determined molar enthalpies of reaction DrHm(cal). These values were then used in conjunction with an equilibrium model to calculate values of the standard molar enthalpies for chemical reference reactions that correspond to the above overall biochemical reactions.

Citation

Journal of Chemical Thermodynamics

Volume

37

Issue

7

Pub Type

Journals

Keywords

3-indoleacetonitrile, alpha-methylbenzeneacetic acid, apparent equilibrium constant, benzeneacetic acid, benzoic acid, benzonitrile, benzylcyanide, enthalpy, indole-3-acetic acid

Citation

Tewari, Y. and Goldberg, R. (2005), Thermodynamics of the Hydrolysis Reactions of Nitriles, Journal of Chemical Thermodynamics (Accessed December 14, 2024)