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Catalysis in nucleophilic aromatic substitution reactions. A reinvestigation of the reaction between 1‐fluoro‐2,4‐dinitrobenzene and n ‐butylamine
Author(s) -
Forlani Luciano,
Bosi Michele
Publication year - 1992
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.610050707
Subject(s) - chemistry , catalysis , amine gas treating , nucleophilic substitution , butylamine , toluene , nucleophilic aromatic substitution , substitution reaction , medicinal chemistry , reaction mechanism , organic chemistry
The reaction between 1‐fluoro‐2,4‐dinitrobenzene and n ‐butylamine in toluene shows a two‐step plot of k obs , values vs the initial values of the concentration of the amine. The usual base‐catalysis mechanism for HF elimination from the zwitterionic intermediate hardly explains this kinetic behaviour and the kinetic effect of addition of salts (and of 2‐hydroxypyridine) to the reaction mixtures at different initial values of the concentration of n ‐butylamine. In contrast, the kinetic behaviours are easily explained by the presence of substrate–amine (or catalyst) interactions on the pathway of the substitution reaction.