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Rapid Bromination Study of Nucleobase-Uracil in Aqueous Medium by Hydrodynamic Voltammetry
Corresponding Author(s) : V.T. Dangat
Asian Journal of Chemistry,
Vol. 28 No. 8 (2016): Vol 28 Issue 8
Abstract
The kinetics and mechanism of the rapid bromination of the nucleobase uracil, by molecular bromine in aqueous medium at pH 7 has been studied employing hydrodynamic voltammetry, NMR and FTIR. The formation of the mono-bromo derivative is found to be a second order rapid reaction. The rate constant, energy of activation and frequency factor for the reaction have been determined and a probable mechanism for the reaction has been proposed.
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- R. Rayala and S.F. Wnuk, Tetrahedron Lett., 53, 3333 (2012); doi:10.1016/j.tetlet.2012.04.081.
- E.D.P. De Robertis, E.M.F. De Robertis Jr, Cell and Molecular Biology, Lippincott Williams and Wilkins, edn 8 (2001).
- M.M. Cox and D.L. Nelson, Lehninger Principles of Biochemistry, W.H. Freeman and Company. New York, edn 5 (2008).
- O.S. Tee and C.G. Berks, J. Org. Chem., 45, 830 (1980); doi:10.1021/jo01293a014.
- H.H. Lee, B.-R. Huang and C.-C. Tzeng, Bioorg. Med. Lett., 9, 241 (1999);
- doi:10.1016/S0960-894X(98)00727-6.
- H. Sajiki, Y. Iida, K. Ikawa, Y. Sawama, Y. Monguchi, Y. Kitade, Y. Maki, H. Inoue and K. Hirota, Molecules, 17, 6519 (2012); doi:10.3390/molecules17066519.
- C.G. Berks, Ph.D. Thesis, The Mechanism of Bromination of Uracil, Concordia University, Montreal, Quebec, Canada (1978).
- W. Bashir, V.T. Borkar and V.T. Dangat, Orient. J. Chem., 31, 2421 (2015); doi:10.13005/ojc/310474.
- S.L. Bonde, V.T. Dangat, R.P. Bhadane and V.S. Joshi, Int. J. Chem. Kinet., 45, 355 (2013); doi:10.1002/kin.20770.
References
R. Rayala and S.F. Wnuk, Tetrahedron Lett., 53, 3333 (2012); doi:10.1016/j.tetlet.2012.04.081.
E.D.P. De Robertis, E.M.F. De Robertis Jr, Cell and Molecular Biology, Lippincott Williams and Wilkins, edn 8 (2001).
M.M. Cox and D.L. Nelson, Lehninger Principles of Biochemistry, W.H. Freeman and Company. New York, edn 5 (2008).
O.S. Tee and C.G. Berks, J. Org. Chem., 45, 830 (1980); doi:10.1021/jo01293a014.
H.H. Lee, B.-R. Huang and C.-C. Tzeng, Bioorg. Med. Lett., 9, 241 (1999);
doi:10.1016/S0960-894X(98)00727-6.
H. Sajiki, Y. Iida, K. Ikawa, Y. Sawama, Y. Monguchi, Y. Kitade, Y. Maki, H. Inoue and K. Hirota, Molecules, 17, 6519 (2012); doi:10.3390/molecules17066519.
C.G. Berks, Ph.D. Thesis, The Mechanism of Bromination of Uracil, Concordia University, Montreal, Quebec, Canada (1978).
W. Bashir, V.T. Borkar and V.T. Dangat, Orient. J. Chem., 31, 2421 (2015); doi:10.13005/ojc/310474.
S.L. Bonde, V.T. Dangat, R.P. Bhadane and V.S. Joshi, Int. J. Chem. Kinet., 45, 355 (2013); doi:10.1002/kin.20770.