KINETICS AND MECHANISM OF THE OXIDATION OF SUBSTITUTED BENZALDEHYDES WITH BIS(PYRIDINE) SILVER PERMANGANATE
Jayshree Banerji, László Kótai, Pradeep K. Sharma,K.K. Banerji*.
Abstract
The oxidation of thirty-six ortho-, meta- and para-substituted benzaldehydes by bis(pyridine)silver permanganate (BPSP) resulted in the formation of the corresponding benzoic acids. The reaction is first order with respect to both BPSP and aldehydes. The reaction is catalyzed by hydrogen ions. The rate of reaction increases with an increase in the amount of acetic acid in the solvent. The correlation analyses of the rate of oxidation of thirty-six aldehydes were performed in terms of Charton’s LDR and LDRS equations. The rate of oxidation of meta-and para-substituted benzaldehydes showed excellent correlation with Charton's LDR equation. The rates of ortho-compounds showed excellent correlation with LDRS equation. The oxidation of para-compounds is more susceptible to the delocalization effect. The oxidation of ortho- and meta-compounds exhibited a greater dependence on the field effect. The polar reaction constants are negative indicating an electron-deficient centre in the rate-determining step. A mechanism involving a rate determining hydride transfer from the aldehyde to the protonated BPSP has been proposed.
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