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Effect of acetonitrile–water mixtures on the reaction of dinitrochlorobenzene and dinitrochlorobenzotrifluoride with hydroxide ion

✍ Scribed by N. M. El-Mallah; S. A. Senior; G. M. Nabil; M. Sh. Ramadan; E. A. Hamed

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
208 KB
Volume
42
Category
Article
ISSN
0538-8066

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✦ Synopsis

Abstract

The kinetics of alkaline hydrolysis of 2‐chloro‐3,5‐dinitrobenzotrifluoride 1 and 1‐chloro‐2,4‐dinitrobenzene 2 were studied in various acetonitrile–water (AN–H~2~O) mixtures (10–90% w/w) at different temperatures. Thermodynamic parameters Δ__H__^#^ and Δ__S__^#^ show great variation, whereas Δ__G__^#^ appears to vary little with the solvent composition presumably due to compensating variations. The results are discussed in terms of the solvent parameters such as preferential solvation, dielectric constant, polarity/polarizability, and hydrogen bond donor and acceptor parameters. It has been found that the factors controlling the reaction rates are the desolvation of OH^−^, the solvophobicity of the medium, and free water molecules in rich AN mixed solvent. The data showed that the solvatochromic parameters of (AN–H~2~O) mixed solvent are destroyed in the presence of excess OH^−^. © 2010 Wiley Periodicals, Inc. Int J Chem Kinet 42: 453–463, 2010

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