3264-08-2

Rate constants for SN2Ar reactions of 2-chloro-3,5-dinitropyridine (1) with butylamine, glycine, glycylglycine and ethylenediamine monohydrochloride, in water at 1.0 mol dm-3 constant ionic strength and 25 deg C, have been determined.The Broensted β coefficient is 0.51.The reactivities of 1 and 2-chloro-1-methylpyridinium ion (2) with these primary amines were compared using a derived Edwards equation.One could infer that 2 tends to undergo more charge interaction than 1 because of the quaternary nitrogen of the pyridinium ring of 2.A coordination of the substrates, 1, 2 and 4-chloro-1-methylpyridinium ion (3) dependent on the degree of hardness and softness is presented.