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Title: Kinetics and mechanism of the nucleophilic substitution reactions of 2-chloro-1-methylpyridinium iodide with primary and secondary amines
Authors: Awwal, A
Kabir, M
Enamullah, M
Hossain, D
Morshed, M M
Issue Date: Jan-2001
Publisher: NISCAIR-CSIR, India
Abstract: Rate constants for the SN2Ar reactions of 2-chloro-1-methylpyridinium iodide with MeNH2, EtNH2, PrNH2, BuNH2, Me2NH and Et2NH in water, at 1mol dm-3 constant ionic strength and 25°C have been determined. The observed rate of reaction is first order with respect to amine as well as the pyridinium iodide i.e., the overall reaction is second order. The relative reactiv ity of the amines towards the reactions is Me2NH >> MeNH2 > EtNH2 > BuNH2 > PrNH2 > Et2NH. The Bronsted β coefficient is 0.67 and the Taft's correlation coefficient ρ25* is 4.39 for the primary amines. Two oppositely charged species seem to be involved in the transition-state of the substitution reactions. A two-step reaction mechanism is consistent with the observed results in which the formation of an intermediate is believed to be the rate determining step.
Page(s): 32-36
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.40B(01) [January 2001]

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