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http://dx.doi.org/10.14478/ace.2011.22.6.718

A Study for Kinetics and Oxidation Reaction of Substituted Benzyl Alcohols Using 2,4'-Bipyridinium Dichromate  

Kim, Young Sik (Department of Chemical Engineering, Kangwon National University)
Park, Young Cho (Department of Chemical Engineering, Kangwon National University)
Publication Information
Applied Chemistry for Engineering / v.22, no.6, 2011 , pp. 718-722 More about this Journal
Abstract
2,4'-Bipyridinium dichromate [$(C_{10}H_8N_2H)_2Cr_2O_7$] was synthesized by the reaction of 2,4'-bipyridinie with chromium trioxide in $H_2O$. The structure was characterized by IR and ICP analysis. The oxidation of benzyl alcohol using 2,4'-bipyridinium dichromate in various solvents showed that the reactivity increased with the increase in the order of the dielectric constant (${\varepsilon}$), in the order : cyclohexene < chloroform < acetone < N,N'-dimethylformamide. In the presence of hydrochloric acid, 2,4'-bipyridinium dichromate effectively oxidized benzyl alcohol and its derivatives ($p-CH_3$, 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 -0.65 at 303 K. 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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1 K. K. Banerji, Indian J. Chem., 17A, 300 (1979).
2 K. K. Banerji, Bull. Chem. Soc. Japan, 61, 1767 (1988).   DOI
3 J. F. Kuo, Bull. Chem. Soc. Japan, 64, 3059 (1991).   DOI
4 M. K. Mahanti and D. Dey, J. Org. Chem., 55, 5848 (1990).   DOI
5 M. K. Mahanti and I. Nongkynrih, J. Org. Chem., 58, 4925 (1993).   DOI   ScienceOn
6 M. K. Mahanti and I. Nongkynrih, Bull. Chem. Soc. Jpn., 67, 2320 (1994).   DOI   ScienceOn
7 M. K. Mahanti and B. Kuotsu, J. Org. Chem., 61, 8875 (1996).   DOI   ScienceOn
8 H. B. Davis, R. M. Sheets, and W. W. Pandler, Heterocycles, 22, 2029 (1984).   DOI
9 M. R. Pressprich, R, D. Willett, and H. B. Davis, Inorg. Chem., 27, 260 (1988).   DOI
10 I. S. Koo, J. S. Kim, and S. K. An, J. Korean Chem. Soc., 43, 527 (1999).
11 R. Tayebee, J. Korean Chem. Soc., 52, 23 (2008).   DOI   ScienceOn
12 R. Y. Sung, H. Choi, and I. S. Koo, Bull. Korean Chem. Soc., 30, 1579 (1988)
13 Y. S. Kim, H. Choi, and I. S. Koo, Bull. Korean Chem. Soc., 31, 3279 (2010).   DOI   ScienceOn