The mechanisms of nucleophilic substitution reactions of aromatic ethers with amines in benzene

Abstract

The variation of the second-order rate constants with nucleophile concentration has been determined for the following reactions of some aromatic ethers with primary and secondary amines in benzene: 6-methyl-2,4-dinitrophenyl- and 2,6-dinitrophenyl phenyl ethers with piperidine, n-butylamine, morpholine and benzylamine; 2-phenoxy-3,5-dinitropyridine with these four nucleophiles and aniline; and 2,4,6-trinitrophenyl 4-nitrophenyl ether with N-methylaniline. An attempt has been made to rationalise the kinetic forms of these and similar reactions of other aromatic ethers in benzene.