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Title: Mechanism and structure-reactivity correlation in the retroaldol reaction of substituted benzylidenemalononitriles with hydroxide ion
Authors: Shunmugasundaram, A
Jawahar, A
Srinivasan, C
Issue Date: Sep-1997
Publisher: NISCAIR-CSIR, India
Abstract: The kinetics of retroaldol reaction of benzylidenemalononitrile and para-substituted benzylidenemalononitriles with hydroxide ion in 90% methanol-10% water (v/v) mixture have been carried out. The reaction is first order with respect to both benzylidenemalononitrile and hydroxide ion. The rate of the reaction increases with increase in water content in the reaction medium and it is not much affected by the change in ionic strength. Addition of acrylonitrile has no influence on the rate of the reaction. On the basis of the kinetic observations, a suitable mechanism involving the nucleophilic attack of the hydroxide ion on the a-carbon atom and the subsequent cleavage of Cα-Cβ bond is proposed. Effect of substituents on the rate of the reaction shows that electron-attracting substituents accelerate the reaction rate while electron-donating substituents retard it. Satisfactory Hammett correlation has been observed.
Page(s): 789-791
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.36A(09) [September 1997]

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