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http://dx.doi.org/10.5762/KAIS.2011.12.12.5990

Kinetics of the Oxidation of Substituted Benzyl Alcohols using 6-Methylquinolinium Dichromate  

Kim, Young-Sik (Department of Chemical Engineering, Kangwon National University)
Park, Young-Cho (Department of Chemical Engineering, Kangwon National University)
Publication Information
Journal of the Korea Academia-Industrial cooperation Society / v.12, no.12, 2011 , pp. 5990-5996 More about this Journal
Abstract
6-Methylquinolinium dichromate[$(C_{10}H_9NH)_2Cr_2O_7$] was synthesized by the reaction of 6-methylquinoline with chromium trioxide in $H_2O$, and characterized by IR, ICP. The oxidation of benzyl alcohol using 6-methylquinolinium dichromate in various solvents showed that the reactivity increased with the increase of the dielectric constant(${\varepsilon}$), in the order: cyclohexene < chloroform < acetone < N,N- dimethylformamide. In the presence of hydrochloric acid($H_2SO_4$ solution), 6-methylquinolinium dichromate oxidized benzyl alcohol and its derivatives(p-$OCH_3$, m-$CH_3$, H, m-$OCH_3$, m-Cl, m-$NO_2$) smoothly in DMF. Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant(${\rho}$) was -0.67(303K). The observed experimental data was used to rationalize the hydride ion transfer in the rate-determining step.
Keywords
Substituted benzyl alcohol; Hammett reaction constant(${\rho}$); Hydride ion transfer; Rate-determining step;
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Times Cited By KSCI : 7  (Citation Analysis)
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