Catalysis in nucleophilic aromatic substitution reactions. A reinvestigation of the reaction between 1‐fluoro‐2,4‐dinitrobenzene and n‐butylamine

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Abstract
The reaction between 1‐fluoro‐2,4‐dinitrobenzene and n‐butylamine in toluene shows a two‐step plot of kobs, 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.