Relative reactivity and kinetic pattern of aniline and N‐methylaniline as nucleophiles in aromatic substitution (SNAr) reactions
No Thumbnail Available
Date
2004-01-29
Authors
Emokpae, T.A.
Isanbor, C.
Journal Title
Journal ISSN
Volume Title
Publisher
Wiley
Abstract
Kinetic results are reported for the reactions of 4-nitrophenyl-2,4,6-trinitrophenyl
ether 3 with aniline and N-methylaniline in dimethyl sulphoxide, acetonitrile, methanol, and
benzene. The reactions gave the expected 2,4,6-trinitrodiphenylamine and were base catalyzed
in all the solvents. Both nucleophiles showed the same kinetic pattern under the same reaction
conditions but aniline was found to be considerably more reactive than N-methylaniline. The
greater catalytic efficiency of aniline over N-methylaniline is consistent with the proton transfer
mechanism of the base-catalyzed step. Dichotomy of amine effects in aromatic substitution
(SNAr) reactions is discussed.
Description
Keywords
Research Subject Categories::NATURAL SCIENCES::Chemistry::Physical chemistry::Kinetics , Nucleophilic aromatic substitution , Base catalysis
Citation
Emokpae, T. A., & Isanbor, C. (2004). Relative reactivity and kinetic pattern of aniline and N‐methylaniline as nucleophiles in aromatic substitution (SNAr) reactions. International journal of chemical kinetics, 36(3), 188-196.