B. Asghar, M. F. Fathalla, Ezzat A. Hamed
Dec 1, 2009
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0
Influential Citations
13
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Journal
International Journal of Chemical Kinetics
Abstract
The solvent effect on a nucleophilic substitution reaction of 2- and 4-chloro-3,5-dinitrobenzotrifluoride with substituted anilines was studied in methanol, acetonitrile, and toluene at 25°C. This reaction is of second order, except 2-chloro-3,5-dinitrobenzotrifluoride in toluene shows third order. The kA values are found to be dependent on the substituent in aniline and give good Hammett correlations. The obtained ρ values are −4.07 and −4.62, for the reaction of anilines with 2-chloro-3,5-dinitrobenzotrifluoride in methanol and acetonitrile, respectively. The ρ values for the reaction of the anilines with 4-chloro-3,5-dinitrobenzotrifluoride are −3.38, −4.11, and −4.34 in methanol, acetonitrile, and toluene, respectively. The reaction of the former compound with anilines in toluene shows a second order in aniline. The dependence of the reaction on the external base such as DABCO suggests a proton transfer controlling step. © 2009 Wiley Periodicals, Inc. Int J Chem Kinet 41: 777–786, 2009