Journal of the Chemical Society. Perkin transactions II p. 829 - 831 (1980)
Update date:2022-08-05
Topics:
Emokpae, Thomas A.
Eguavoen, Osa
Hirst, Jack
Arrhenius parameters have been measured for the reactions of picryl chloride with the following substituted anilines in acetonitrile: 3-amino- and 3-methyl-aniline, 3-amino-5-nitroaniline, 3-fluoro-5-methylsulphonylaniline, 3-X-5-methylanilines (X=NO2, OMe, CH3, F, Cl, Br, or I) and 3,5-X2-anilines (X = F, Cl, Br, or I).A total of 33 3,5-disubstituted anilines have now been examined for the additivity of substituent effects on the free energy of activation, and it has been shown that with the exception of 3-amino-5-nitroaniline this hypothesis reproduces experimental rate constants within a factor of 2.A rationalization is proposed for the deviations that occur in some cases when more stringent criteria of additivity are used.
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