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Kinetic studies of the N ‐alkylation of secondary amines with 1,2‐dichloroethane
Author(s) -
Yang H.,
Thyrion F. C.
Publication year - 1994
Publication title -
international journal of chemical kinetics
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.341
H-Index - 68
eISSN - 1097-4601
pISSN - 0538-8066
DOI - 10.1002/kin.550260209
Subject(s) - chemistry , diethylamine , 1,2 dichloroethane , ethylenediamine , dichloroethane , amine gas treating , alkylation , medicinal chemistry , reaction rate constant , ion , substitution reaction , elimination reaction , ethanol , organic chemistry , kinetics , catalysis , physics , quantum mechanics
The reactions of 1,2‐dichloroethane with 2‐(ethylamino)ethanol or diethylamine have been investigated in several solvents from 51 to 80°C. A reaction mechanism has been proposed where 1,2‐dichloroethane reacts with the secondary amines in both bimolecular substitution (S N 2) and elimination ( E 2) reactions; the substitution product is rapidly converted in an aziridinium ion and undergoes a consecutive reaction with the starting amine to give a tetrasubstituted ethylenediamine. The rate constants as well as the activation energies of these reactions have been determined. © 1994 John Wiley & Sons, Inc.