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Title: Substituent effect in the oxidation of cinnamic acids by quinolinium dichromate
Authors: Aruna, K
Manikyamba, P
Issue Date: Oct-1995
Publisher: NISCAIR-CSIR, India
Abstract: Oxidation of cinnamic acid and substituted cinnamic acids by quinolinium dichromate is first order each in [oxidant]and [cinnamic acid]. The reaction is acid catalysed, and Hammett's acidity function H0 is used as a measure of the acidity of the medium. A medium of low dielectric constant favours the oxidation process. Among the substituents used for the oxidation process, the order of reactivity is found to be p-OCH3 » p-CH3> H > p-Cl > m- Cl > m-NO2> p-NO2 CorreIation of log k2 with σ+ gives a linear plot with a negative slope and the reaction constant ρ+ is found to be – 0.53. The mechanism proposed involves a slow attack of (QH)H2CrO4 on cinnamic acid forming a cyclic complex which ultimately decomposes to give benzaldehyde.
Page(s): 822-825
ISSN: 0975-0975(Online); 0376-4710(Print)
Appears in Collections:IJC-A Vol.34A(10) [October 1995]

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