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Title: Non-linear structure-reactivity correlation in the addition reaction of n- butylamine to para- substitutedethyl α-cyanocinnamates
Authors: Radhakrishnan, K
Srinivasan, C
Shunmugasundaram, A
Thanulingam, T Lekshmana
Issue Date: May-1996
Publisher: NISCAIR-CSIR, India
Abstract: The study of kinetics of addition of n-butylamine to a number of para- substitutedethyl a-cyanocinnamates in acetonitrile reveals that the reaction is first order in the substrate and the order In nucleophile varies with the nature of the para-substituent. The analysis of the rate data of the various para- substituted ethyl α-cyanocinnamates in terms of the Hammett equation gives a non-linear concavedown type of curve. A stepwise mechanism involving the formation of zwitterionic addition complex in an equilibrium step followed by conversion into the reaction product via a proton transfer In two routes, viz., non-catalytic and by amine catalysed, has been proposed. The non-linear structure-reactivity correlation has been accounted for by the change in rate-controlling step.
Page(s): 401-407
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.35A(05) [May 1996]

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