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Correlation analysis of reactivity in the addition of substituted benzylamines to ethyl α-cyanocinnamate

✍ Scribed by Neeta Jalani; Seema Kothari; Kalyan K. Banerji

Publisher: John Wiley and Sons
Year: 1996
Tongue: English
Weight: 356 KB
Volume: 28
Category: Article
ISSN: 0538-8066
DOI: 10.1002/(sici)1097-4601(1996)28:3<165::aid-kin2>3.0.co;2-t

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✦ Synopsis

The kinetics o f addition of a number of ortho-. rneta-, and para-substituted benzylarnines to ethyl a-cyanocinnamate [ECC) in acetonitrile have been studied. T h e reaction is First-order with respect to the amine and ECC. The rates of reaction of rneta-and para-substituted benzylamines showed excellent correlations with Taft's crI and c r i . and with crI and [TP values, respectively The reaction of the ortho-compounds showed a very good correlation with Charton's tripararnetric equation The reaction is subject to steric hindrance by the orthosubstituents. A mechanism involving formation of a zwitterionic intermediate in a slow step followed by a Fast proton transfer has been proposed 0 1996 lohn Wiley & Sons. Inc

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