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http://dx.doi.org/10.14478/ace.2015.1021

A Study for Kinetics and Oxidation Reaction of Substituted Benzyl Alcohols Using Cr(VI)-6-Methylquinoline  

Park, Young Cho (The School of General Studies, Kangwon National University)
Kim, Young Sik (The School of General Studies, Kangwon National University)
Publication Information
Applied Chemistry for Engineering / v.26, no.3, 2015 , pp. 372-376 More about this Journal
Abstract
6-MQCC (Cr(VI)-6-methylquinoline) complex was synthesized by the reaction of 6-methylquinoline with chromium(VI) trioxide in 6 M HCl. The structure was characterized using IR (Infrared Spectroscopy) and ICP (Inductively Coupled Plasma) analysis. The oxidation of benzyl alcohol using 6-MQCC in various solvents showed that the reactivity increased with the increase of the dielectric constant, in descending order of DMF > acetone > chloroform > cyclohexene. In the presence of DMF solvent with acidic catalyst such as sulfuric acid ($H_2SO_4$), 6-MQCC oxidized benzyl alcohol (H) and its derivatives ($p-OCH_3$, $m-CH_3$, $m-OCH_3$, m-Cl, $m-NO_2$) were effectively oxidized. Electron-donating substituents accelerated the reaction rate, whereas electron acceptor groups retarded the reaction rate. The Hammett reaction constant (${\rho}$) was -0.69 (308 K). The observed experimental data was used to rationalize the fact that the hydride ion transfer occurred at the rate-determining step.
Keywords
6-MQCC; substituted benzyl alcohol; Hammett reaction constant (${\rho}$); hydride ion transfer; rate-determining step;
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Times Cited By KSCI : 2  (Citation Analysis)
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