The mechanism of aromatic nucleophilic substitution reactions in protic solvents. The reations of aniline, N-methylaniline, n-butylamine, and piperidine with some nitroaryl phenyl ethers in methanol

In methanol, the reactions of aniline with 2-phenoxy-3,5-dinitropyridine, phenyl 2,4,6-trinitrophenyl ether, and 4-nitrophenyl 2,4,6-trinitrophenyl ether and the last-named substrate with N-methylaniline are general-base catalysed. The reaction of 2,6-dinitrophenyl phenyl ether with n-butylamine is not base catalysed, but its reaction with piperidine is specific-base catalysed. The results are discussed in terms of the mechanism of aromatic nucleophilic substitution reactions in protic solvents.