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http://dx.doi.org/10.5762/KAIS.2012.13.7.3252

A Study for Mechanism and Oxidation Reaction of Substituted Benzyl Alcohols by 2,2'-Bipyridinium Chlorochromate  

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.13, no.7, 2012 , pp. 3252-3260 More about this Journal
Abstract
2,2'-Bipyridinium chlorochromate[$C_{10}H_8N_2HCrO_3Cl$] was synthesized by the reaction of 2,2'- bipyridine with chromium(VI) trioxide in 6M HCl. The structure was characterized by IR and ICP analysis. The oxidation of benzyl alcohol using 2,2'-bipyridinium chlorochromate in various solvents showed that the reactivity increased with the increase in the order of the dielectric constant(${\varepsilon}$), in the order: cyclohexene< chloroform, H, m-Br, $m-NO_2$) in N,N'-dimethylformamide. Electron-donating substituents accelerated the reaction, whereas electron acceptor groups retarded the reaction. The Hammett reaction constant(${\rho}$) was -0.64(303K). The oxidation reactivity of alcohols can be a useful factor to study about physical properties such as thermal stability, when the polysilsesquioxane solution is ready for an applying coating agent. The observed experimental data was used to rationalized 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 : 3  (Citation Analysis)
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