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Copyright (c) 2014 Raed Ghanem
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Kinetics Study of the Chemical Oxidation of Pindolol by Peroxodiphosphate
Corresponding Author(s) : Raed Ghanem
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
In order to analyze the selectivity of the oxidizing agent on the chemical oxidation of pindolol in methanol/acidic media, the reaction of pindolol by peroxodiphosphate [PDP] in acidic media was studied. It was found that the reaction mechanism is comparable with other peroxides, however, reaction products are different depending on the acidity condition, at low acid concentration, oxipindolol is formed through acid catalyzed transformation of the indonlonic intermediate while at high acid concentration, the intermediate can react through competing parallel reaction to produce three products (oxipindolol, dioxipindolol and indigo form of pindolol) for the 1-PDP reaction. It is also found that, under present experimental conditions, neutral H4P2O8 is the active species involved in the oxidation process. Comparison of kinetics behaviour of the 1-PDP reaction with other peroxides were also investigated and we conclude that H4P2O8 is more reactive than H2S2O8 while HS2O8– is better electrophilic compared to the H3P2O8–.
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- E. Fernandes, A. Gomes, D. Costa and J.L.F.C. Lima, J. Life Sci., 77, 1983 (2005).
- A. Napolitano, M. d'Ischia and G. Prota, Tetrahedron, 44, 7265 (1988).
- R. Ghanem and A. Hadi, J. Solution Chem., 38, 641 (2009).
- W. Houlihan, W. Remers and R. Brown, The Chemistry of Heterocyclic Compounds, Wiley, pp. 153-300 (1972).
- M. Mahrous, A.S. Issa and N.S. Ahmed, Talanta, 39, 69 (1992).
- S. Khalil and N. Borham, J. Pharm. Biomed. Anal., 22, 235 (2000).
- S. Al-Ghannam, J. Pharm. Biomed. Anal., 40, 151 (2006).
- C. Gazpio, M. Sanchez, A. Zornoza, C. Martin, C. Martinez-Oharriz and I. Velaz, Talanta, 60, 477 (2003).
- A. Gölcü, C. Yücesoy and S. Serin, Synth. React. Inorg. Metal Org. Chem., 34, 1259 (2004).
- C. Gazpio, M. Sánchez, I. García-Zubiri, I. Vélaz, C. Martínez-Ohárriz, C. Martín and A. Zornoza, Pharmaceut. Biomed. Anal., 37, 487 (2005).
- C. Carmona, R. Ghanem, M. Balon, P. Guardado and M.A. Munoz, J. Chem. Soc., Perkin Trans. 2, 839 (2000).
- M. Balon, M. Munoz, P. Guardado, J. Hidalgo and C. Carmona, J. Org. Chem., 58, 7469 (1993).
- R. Ghanem, C. Carmona, M.A. Munoz, P. Guardado and M. Balon, J. Chem. Soc., Perkin Trans. II, 2197 (1996).
- E. Wenkert, J.S. Bindra, C.-J. Chang, D.W. Cochran and F.M. Schell, Alkaloids Acc. Chem. Res., 7, 46 (1974).
- A.H. Jackson, R.T. Jenkins, M. Grinstein, A.-M.F. de Sancovich and H.A. Sancovich, Clin. Chim. Acta, 172, 245 (1988).
- R. Eaton and P.J. Chapman, Bacteriology, 177, 6983 (1995).
- M. Crutchfield and J. Edwards, J. Am. Chem. Soc., 82, 3533 (1960).
- L.M. Bharadwaj, D.N. Sharma and Y.K. Gupta, Inorg. Chem., 15, 1695 (1976).
- J. Edwards, Peroxide Reaction Mechanisms, Interscience, New York (1962).
- E.J. Behrman and J.O. Edwards, Progress in Physical Organic Chemistry, p. 4 (1967).
References
E. Fernandes, A. Gomes, D. Costa and J.L.F.C. Lima, J. Life Sci., 77, 1983 (2005).
A. Napolitano, M. d'Ischia and G. Prota, Tetrahedron, 44, 7265 (1988).
R. Ghanem and A. Hadi, J. Solution Chem., 38, 641 (2009).
W. Houlihan, W. Remers and R. Brown, The Chemistry of Heterocyclic Compounds, Wiley, pp. 153-300 (1972).
M. Mahrous, A.S. Issa and N.S. Ahmed, Talanta, 39, 69 (1992).
S. Khalil and N. Borham, J. Pharm. Biomed. Anal., 22, 235 (2000).
S. Al-Ghannam, J. Pharm. Biomed. Anal., 40, 151 (2006).
C. Gazpio, M. Sanchez, A. Zornoza, C. Martin, C. Martinez-Oharriz and I. Velaz, Talanta, 60, 477 (2003).
A. Gölcü, C. Yücesoy and S. Serin, Synth. React. Inorg. Metal Org. Chem., 34, 1259 (2004).
C. Gazpio, M. Sánchez, I. García-Zubiri, I. Vélaz, C. Martínez-Ohárriz, C. Martín and A. Zornoza, Pharmaceut. Biomed. Anal., 37, 487 (2005).
C. Carmona, R. Ghanem, M. Balon, P. Guardado and M.A. Munoz, J. Chem. Soc., Perkin Trans. 2, 839 (2000).
M. Balon, M. Munoz, P. Guardado, J. Hidalgo and C. Carmona, J. Org. Chem., 58, 7469 (1993).
R. Ghanem, C. Carmona, M.A. Munoz, P. Guardado and M. Balon, J. Chem. Soc., Perkin Trans. II, 2197 (1996).
E. Wenkert, J.S. Bindra, C.-J. Chang, D.W. Cochran and F.M. Schell, Alkaloids Acc. Chem. Res., 7, 46 (1974).
A.H. Jackson, R.T. Jenkins, M. Grinstein, A.-M.F. de Sancovich and H.A. Sancovich, Clin. Chim. Acta, 172, 245 (1988).
R. Eaton and P.J. Chapman, Bacteriology, 177, 6983 (1995).
M. Crutchfield and J. Edwards, J. Am. Chem. Soc., 82, 3533 (1960).
L.M. Bharadwaj, D.N. Sharma and Y.K. Gupta, Inorg. Chem., 15, 1695 (1976).
J. Edwards, Peroxide Reaction Mechanisms, Interscience, New York (1962).
E.J. Behrman and J.O. Edwards, Progress in Physical Organic Chemistry, p. 4 (1967).