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Oxidation of Indole by Peroxomonosulfate in Acetic Acid Medium: A Kinetic and Antibacterial Study
Corresponding Author(s) : K. Muniyappan
Asian Journal of Chemistry,
Vol. 29 No. 5 (2017): Vol 29 Issue 5
Abstract
Kinetics of oxidation of indole by peroxomonosulfate (PMS) has been studied at 283 to 308 K in aqueous acetic acid medium. The reaction follows a total second order, first order each with respect to [Indole] and [PMS]. The rate of the reaction was not affected by added [H+]. Variation of ionic strength (μ) had no influence on the rate. There was no solvent effect when increase the percentage of acetic acid. There was no polymerization occur in reaction pathway. Thermodynamic parameters such as free energy of activation (DE#), enthalpy of activation (DH#) and entropy of activation (DS#) have been evaluated. The most plausible mechanism scheme proposed by these kinetic observations and the antibacterial activity was carried out by agar diffusion method.
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- G. Chandramohan, S. Kalyanasundharam and R. Renganathan, Int. J. Chem. Kinet., 34, 569 (2002); https://doi.org/10.1002/kin.10060.
- S. Kalyanasundharam, G. Chandramohan, M. Suresh, V. Anbazhagan, S. Lavanya and R. Renganathan, Int. J. Chem. Kinet., 37, 355 (2005); https://doi.org/10.1002/kin.20090.
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- R. Pressey, J. Mol. Catal., 70, 243 (1991); https://doi.org/10.1016/0304-5102(91)80165-Y.
- R.L. Hinman and J. Lang, Biochemistry, 4, 144 (1965); https://doi.org/10.1021/bi00877a023.
- (a) M. Amir, N. Dhar and S.K. Tiwari, Indian J. Chem., 36B, 96 (1997); (b) J. Bergman, E. Koch and B. Pelcman, Tetrahedron Lett., 36, 3945 (1995); https://doi.org/10.1016/0040-4039(95)00648-V.
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- S. Biswal, U. Sahoo, S. Sethy, H.K.S. Kumar and M. Banerjee, Asian J. Pharm. Clin. Res., 5, 1 (2012).
- J. Chen, S. Safe and L. Bjeldanes, Biochem. Pharmacol., 51, 1069 (1996); https://doi.org/10.1016/0006-2952(96)00060-3.
- S. Suzen and E. Buyukbingol, IL Farmaco, 55, 246 (2000); https://doi.org/10.1016/S0014-827X(00)00028-8.
- G. Giagoudakis and S.L. Markantonis, Pharmacotherapy, 25, 18 (2005); https://doi.org/10.1592/phco.25.1.18.55618.
- E. Buyukbingo, S. Suzen and G. Klopman, IL Farmaco, 49, 6 (1994).
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- C. Carmona, M. Balon, M.A. Munoz, P. Guardado and J. Hidalgo, J. Chem. Soc., Perkin Trans. 2, 331 (1995); https://doi.org/10.1039/P29950000331.
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- P. Maruthamuthu and P. Neta, J. Phys. Chem., 81, 937 (1977); https://doi.org/10.1021/j100525a001.
- K.J. Laidler, Chemical Kinetics, Tata-McGraw Hill, New Delhi, p. 229 (1965).
- S.S. Anis, J. Chim. Phys., 89, 659 (1992).
- A.H. Jackson and P.P. Lynch, J. Chem. Soc., Perkin Trans. 2, 1215 (1987); https://doi.org/10.1039/p29870001215.
- W. Ando, H. Miyazaki and T. Akasaka, J. Chem. Soc. Chem. Commun., 518 (1983); https://doi.org/10.1039/c39830000518.
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References
G. Chandramohan, S. Kalyanasundharam and R. Renganathan, Int. J. Chem. Kinet., 34, 569 (2002); https://doi.org/10.1002/kin.10060.
S. Kalyanasundharam, G. Chandramohan, M. Suresh, V. Anbazhagan, S. Lavanya and R. Renganathan, Int. J. Chem. Kinet., 37, 355 (2005); https://doi.org/10.1002/kin.20090.
J.F. Harrod and C. Guerin, Inorg. Chim. Acta, 37, 141 (1979); https://doi.org/10.1016/S0020-1693(00)95535-X.
R. Pressey, J. Mol. Catal., 70, 243 (1991); https://doi.org/10.1016/0304-5102(91)80165-Y.
R.L. Hinman and J. Lang, Biochemistry, 4, 144 (1965); https://doi.org/10.1021/bi00877a023.
(a) M. Amir, N. Dhar and S.K. Tiwari, Indian J. Chem., 36B, 96 (1997); (b) J. Bergman, E. Koch and B. Pelcman, Tetrahedron Lett., 36, 3945 (1995); https://doi.org/10.1016/0040-4039(95)00648-V.
G.S. Gadaginamath and A.S. Shyadligeri, Indian J. Chem., 34B, 1059 (1995).
A.T. Al-Kazwini, P. O’ Neill, G.E. Adams, R.B. Cundall, A. Junino and J. Maignan, J. Chem. Soc., Perkin Trans. 2, 657 (1992); https://doi.org/10.1039/p29920000657.
S.N. Krylov and H.B. Dunford, J. Phys. Chem., 100, 913 (1996); https://doi.org/10.1021/jp9522270.
S. Biswal, U. Sahoo, S. Sethy, H.K.S. Kumar and M. Banerjee, Asian J. Pharm. Clin. Res., 5, 1 (2012).
J. Chen, S. Safe and L. Bjeldanes, Biochem. Pharmacol., 51, 1069 (1996); https://doi.org/10.1016/0006-2952(96)00060-3.
S. Suzen and E. Buyukbingol, IL Farmaco, 55, 246 (2000); https://doi.org/10.1016/S0014-827X(00)00028-8.
G. Giagoudakis and S.L. Markantonis, Pharmacotherapy, 25, 18 (2005); https://doi.org/10.1592/phco.25.1.18.55618.
E. Buyukbingo, S. Suzen and G. Klopman, IL Farmaco, 49, 6 (1994).
(a) R.J. Kennedy and A.M. Stock, J. Org. Chem., 25, 1901 (1960); https://doi.org/10.1021/jo01081a019. (b) R. Somuthevan, R. Renganathan and P. Maruthamuthu, Inorg. Chim. Acta Lett., 45, 165 (1980); https://doi.org/10.1016/S0020-1693(00)80133-4. (c) C.A. Bunton, H.J. Foroudian and A. Kumar, J. Chem. Soc., Perkin Trans. II, 33 (1995); https://doi.org/10.1039/p29950000033. (d) A.A. Jameel and P. Maruthamuthu, J. Indian Chem. Soc., 75, 368 (1998).
C. Carmona, M. Balon, M.A. Munoz, P. Guardado and J. Hidalgo, J. Chem. Soc., Perkin Trans. 2, 331 (1995); https://doi.org/10.1039/P29950000331.
R. Ghanem, C. Carmona, M.A. Muñoz, P. Guardado and M. Balón, J. Chem. Soc., Perkin Trans. 2, 2197 (1996); https://doi.org/10.1039/P29960002197.
M. Balon, M. Munoz, P. Guardado, J. Hidalgo and C. Carmona, J. Org. Chem., 58, 7469 (1993); https://doi.org/10.1021/jo00078a027.
P. Maruthamuthu and P. Neta, J. Phys. Chem., 81, 937 (1977); https://doi.org/10.1021/j100525a001.
K.J. Laidler, Chemical Kinetics, Tata-McGraw Hill, New Delhi, p. 229 (1965).
S.S. Anis, J. Chim. Phys., 89, 659 (1992).
A.H. Jackson and P.P. Lynch, J. Chem. Soc., Perkin Trans. 2, 1215 (1987); https://doi.org/10.1039/p29870001215.
W. Ando, H. Miyazaki and T. Akasaka, J. Chem. Soc. Chem. Commun., 518 (1983); https://doi.org/10.1039/c39830000518.
K.R. Meenal and G. Ramanivimala, J. Indian Chem. Soc., 71, 609 (1994).
K.R. Meenal and G. Ramanivimala, J. Indian Chem. Soc., 74, 43 (1997).