1258542-73-2Relevant academic research and scientific papers
Solvent and substituent effects on the reaction of 2- and 4-chloro-3,5-dinitrobenzotrifluorides with substituted anilines
Asghar, Basim H.M.,Fathalla, Magda F.,Hamed, Ezzat A.
, p. 777 - 786 (2009)
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.
