ISSN:
0538-8066
Keywords:
Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The kinetics of addition of a number of ortho-, meta-, and para-substituted benzylamines to ethyl α-cyanocinnamate (ECC) in acetonitrile have been studied. The reaction is first-order with respect to the amine and ECC. The rates of reaction of meta- and para-substituted benzylamines showed excellent correlations with Taft's σ1 and σR0, and with σ1 and σRBA values, respectively. The reaction of the ortho-compounds showed a very good correlation with Charton's triparametric equation. The reaction is subject to steric hindrance by the ortho-substituents. A mechanism involving formation of a zwitterionic intermediate in a slow step followed by a fast proton transfer has been proposed. © 1996 John Wiley & Sons, Inc.
Additional Material:
5 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/kin.2
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