Journal of Organic Chemistry p. 4764 - 4767 (1986)
Update date:2022-08-10
Topics:
Banerji, Kalyan K.
The oxidation of eighteen meta- and para-substituted benzaldehydes by N-bromobenzamide (NBB), to the corresponding benzoic acid, is first order with respect to the aldehyde, NBB, and hydrogen ion.The oxidation of benzaldehyde exhibited a substantial primary kinetic isotope effect(kH/kD = 5.3 +/- 0.1).Addition of benzamide has no effect on the reaction rate. (PhCONH2Br)+ has been postulated as the reactive oxidizing species.The rates of the oxidation of meta- and para-substituted benzaldehydes were separately correlated in Taft's and Swain's dual substituent parameter equations.For para-substituted aldehydes, the best correlation was obtained with ?1 and ?R+ values, while meta-substituted compounds correlate with ?1 and ?R0 values.The reaction constants have negative values.A mechanism involving transfer of a hydride ion from the aldehyde to the oxidant, in the rate-determining step, has been proposed.
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