Oxidation of Indole - 3 - Propionic Acid by Peroxodisulphate in T - Butanol - A Kinetic Study

Authors(2) :-K. RamKumar, S. Thanga Malathi

Kinetic investigation on the oxidation of Indole - 3 - Propionic acid by Peroxodisulphate in t - Butanol, have been studied in the effect of temperature, solvent, ionic strength, stoichiometry of the reaction and to the influence of radical scavengers and to find the nature of the species involved in the oxidation process. Indole and its derivatives are important class of bio – organic molecules exhibit a wide range of reactivity such as oxidation, nitration, electron transfer, substitution in many cases. It has much attention because they have antibacterial, antitumor, antifungal and anti tuberculosis properties etc., since biological oxidation form an integral component research, the present research work focus on the oxidation of certain Indole derivative by peroxodisulphate which has been proved to be a good oxidant.

Authors and Affiliations

K. RamKumar
B. T. Assistant Science, Maruthu Pandora High. Sec. School, Narikkudi, Virdhunagar, Tamil Nadu, India
S. Thanga Malathi
Department of Biochemistry, Mohamed Sathak College of Arts and Science, Sholinganallur, Tamil Nadu, India

Oxidation, Kinetic Study, Indole - 3 - Propionic Acid.

  1. T.A.Turney, "Oxidation Mechanism", Butterworths, London P. 6 (1965).
  2. J.March "Advanced Organic Chemistry", Wiley Eastern Limited, New Delhi P.1048 (1987).
  3. A.J.Birch and D.Nasipuri, Tetrahedron, 6, 148 (1959).
  4. J.Rocek, J.Am.chem..soc., 96, 1522 (1974).
  5. J.Rocek, J.Am.chem..soc., 96, 2840 (1974).
  6. R.B.Woodward, N.L.Wendler and F.J.Brutschy, J.Am.Chem.soc., 67, 1425 (1945).
  7. E.Pfeil, Chem. Ber., 84,229(1951).
  8. C.B.Polland and D.C.Young, J,org, chem.,16,661.
  9. S.J.Angyal and R.C.Rassack J.Chem. soc.,2700(1949).
  10. S.J.Angyal, "Organic reaction" vol. VIII, P.Adamn Wiley, New york P,197 (1954).
  11. M.Prasada Rao, B.Sethuram and T.Navneeth Rao,Cur, Sci., 48, 65 (1979).
  12. L.P.Hammett, Physical Organic Chemistry, Mc Graw Hill, New York, P.350 (1940).
  13. K.K.Banerji, J,chem..soc., Perkin Trans.II, 345 (1973).
  14. P.Aukett and R.L.Barker, J,chem..soc.,Perkin Trans, II, 568 (1972).
  15. D.G.Lec and M.V.D.Engh, Can.J.Chem., 50,2000 (1972).
  16. P.Veersomaiah, K.Balreddy, B.Sethuram and T.Navreeth Rao, Indian J.Chem.,27A,876 (1988).
  17. K.B.will berg and R.Stewart, J.Am.Chem.Soc., 77, 1786 (1955).
  18. G.J. Buist and C.A. Brunton, J. Chem. Soc., B, 2117 (1971).
  19. C.G. Swain, R.A. Wiles and R.F.W. Badar, J. Am. Chem. Soc., 83, 1945 (1961).
  20. H.H. Jaffee, Chem. Rev., 53, 191 (1953).
  21. C.Walling and B. Jacknow, J. Am. Chem. Soc., 82, 6113 (1960).
  22. E.S. Lewis, In : "Investigation of Rates and Mechanisms" Part I, 3rd edn., E.S. Lewis (ed.), John Wiley & Sons, New York, Vol.VI, p.3 (1974).
  23. W.K. Wilmarth and A. Haim in "Peroxide Reaction Mechanism", ed. J.O. Edwards, Wiley-Interscience, New York, p.175 (1962).
  24. C. Marsh and J.O. Edwards, "Progress in Reaction Kinetics", Pergamon Press, p.60 (1989).
  25. L. Pauling, "The Nature of Chemical Bond", Oxford and IBH Publishing Co., Calcutta, p.85 (1969).
  26. J.A. Kerr, Chem, Rev., 66, 465 (1966).
  27. R.Curci and J.O. Edwards, in "Organic Peroxides", ed. D.Swern, Wiley-Interscience, New York, Vol.1., P.212 (1970).
  28. L.S. Silbert in "Organic Peroxides", ed. D.Swern, Wiley-Interscience, New York, Vol.2. p.637 (1971).
  29. J.O. Edwards, Chem. Rev., 50, 455 (1952).
  30. M.Berthelot, Ann. Chim. Phys., 14, 345 (1878).
  31. I.M.Kolthoff and I.K.Miller, J. Am. Chem. Soc., 73, 3055 (1951).
  32. J.D’Ans and W.Frienderich, Ber., 43, 1880 (1910).
  33. D.A.House, Chem. Rev., 62, 185 (1962).
  34. E.J.Behram and J.E. Mclssac, Jr., in "Mechanisms of Reactions of Sulphur Compounds", N.Kharasch, Ed., 2nd edn., Intrascience Pub., Los Angeles, p.193 (1968).
  35. F.Minisci, A. Citterio and C.Giordano, Acc. Chem. Res., 16, 27 (1983).
  36. W.M.Latimer, "The Oxidation States of the Elements and their Potentials in Aqueous Solution", Prentice Hall, New York, N.Y., p.78 (1952).
  37. G.J.Buist, in. ‘Comprehensive Chemical Kinetics’ Vol. VI, Eds., C.H.Bamford and C.F.H. Tipper, Elsevier, New York, p.456 (1972) and references cited therein.
  38. E.J.Behrman and P.P.Walker, J. Am. Chem. Soc., 84, 3454 (1962).
  39. E.J.Behrman, J. Am. Chem. Soc., 85, 3478 (1963).
  40. C.Srinivasan and S.Rajagopal, Curr. Sci., 46, 669 (1977).
  41. G.P.Panigrahi and R.Panda, Indian J. Chem., 15A, 1070 (1977).
  42. E.J.Behrman, J. Am. Chem. Soc., 89, 2424 (1967).
  43. N.Venkatasubramanian and A.Sabesan, Can. J. Chem., 47, 3710 (1969).
  44. C.Srinivasan, S.Perumal and N.Arumugam, Indian J. Chem., A, 19A,160 (1980).
  45. E.J.Behrman and D.M.Behrman, J. Org. Chem., 43, 4551 (1978).
  46. G.Mark, M.N.Schuchmann, H.P.Schuchmann and C.Y. Sonntag, J. Photochem. Photobiol. A : Chem., 55, 157 (1990).
  47. L.Dogliotti and E.Hayon, J.Phys. Chem., 71(8), 2511 (1967).
  48. I.M.Kolthoff, E.J.Meehan and E.M.Carr,.J.Am.Chem. Soc., 75, 1439 (1953).
  49. C.Srinivasan, S.Perumal and N.Arumugam, J.Chem. Soc. Perkin Trans. II, 1855 (1985).
  50. K.R.Meenal and T.S.Jani Bai, J. Indian Chem. Soc., 71, 117 (1994).
  51. M.Balon, M.Munoz, P.Guardado, J.Hidalgo, and C.Carmona, J.Org. Chem., 58, 7469 (1993).
  52. M.B.Almedia and M.A.M. Perez, J.Chem. Soc. Perkin Trans. II, 1065 (1988).
  53. N.Arumugam, C.Srinivasan and P.Kuthalingam, Indian J. Chem., 16A, 478 (1978).
  54. C.Srinivasan, P.Kuthalingam and N.Arumugam, Can. J.Chem., 56 (24), 3043 (1978).
  55. E.Howard JR., and L.S.Levitt, J. Am. Chem. Soc., 75, 6170 (1953).
  56. S.Padma and M.Santappa, Proc. Indian Acad. Sci. Sec. A, 69, 7 (1969).
  57. H.Singh, L.R. Verma and B.D.Kansal, J.Indian Chem. Soc.,
  58. Vol. LVI, 37 (1979).
  59. K.Kumar and L.K.Saxena, J. Indian Chem. Soc., 47 (5), 435 (1970).
  60. R.L.Eager and C.A. Winkler, Can. J. Res., 26 (B), 527 (1948)
  61. G.Chandra and S.N.Srinivastava, J. inorg. Nucl. Chem., 34, 197 (1972).
  62. S.P.Srivastava, G.L. Maheshwari and S.K.Singhal, Indian.
  63. J. Chem., 12, 72 (1974).
  64. N.C.Khandual and P.L.Nayak, J. Indian Chem. Soc., Vol. L, 786, (1973).
  65. N.C.Khandual, React, Kinet, Catal. Lett., 41(2), 363 (1990).
  66. J.M.Anderson and J.K.Kochi, J. Am. Chem. Soc., 92(6), 1651 (1970).
  67. S.P.Srivastava and A.K.Shukla, Indian J. Chem., 15A, 603 (1977).
  68. N.C.Khandual and P.L.Nayak, J.Indian Chem. Soc., Vol.L, 194 (1973).
  69. J.F.Harrod and C.Guerin, Inorg. Chem. Acta., 37, 141 (1979)
  70. T.Ohnuma, H.Kasuya, Y.Kimura and Y.Ban, Heterocycles, 17,
  71. 377 (1982)
  72. Kanchugarakoppal S.Rangappa and Daniel T.Esterline, Polyhetron, 12, 1719 (1993).
  73. P.Capdevielle and M.Maumy, Tetrahedron Lett., 34 (18), 2953 (1993).
  74. A.J.Lawson, B.C.Challiss, J.Chem.Soc., Perkin Trans. II (1973).
  75. E.M.J.Gillan, L.M.Notley, H.Cai, J.J.De Voss, and F.P Guengerich, Biochem., 39, 13817 (2000).
  76. R.Ghanem, C.Carmona, M.A.Munoz, P.Guardado and Manuel Balon J.Chem.Soc., Perkin Trans. II, 2197(1996).
  77. R.L.Hinman and J.Lang, Biochem., 4 (1), 144 – 158 (1965).
  78. M.Laronze, J.M.Laronze, C.Nemes and J.Sapi, Eur. J.Org. Chem., 2285 (1999).
  79. R.Pressey, Journal of Molecular Catalysis, 70, 243 (1991).
  80. Shin Sakai, A.Kubo, K.Katsuura, K.Mochinaga and M.Ezaki, Chem.Pharm Bull., 20 (1), 76 (1972).
  81. L.J.Dolby and D.L.Booth, J.Am.Chem.Soc., 85 (5), 1049 (1966).
  82. C.Bravo, P.Herves, J.Ramon Leis and M.Elena Pena, J.Chem.Soc., Perkin Trans.2, 185, (1992).
  83. A.R.Mount and A.D.Thomson, J.Chem. Soc., Faraday Trans.,
  84. 94 (4), 553 (1998).
  85. Raj K.Bansal, "Heterocyclic Chemistry", Ed.Wiley Eastern Ltd., New Delhi, 215 (1990).
  86. C.Srinivasan, S.Perumal and N.Arumugam, J.Chem. Soc., Perkin Trans II, 1855 (1985).
  87. K.J.P.Orton and A.E.Bradfield, J.Chem. Soc., 960 (1924).
  88. I.M.Kolthoff and E.M.Carr, Anal. Chem., 25, 298 (1953)
  89. K.J. Laidler, "Chemical Kinetics", Tata-McGraw Hill, New Delhi, p.229 (1965).
  90. E.J. Behrman and J.O. Edwards, in Prog. Phys. Org. Chem., 4, 93 (1967).
  91. R. Curci and J.O.Edwards, "Organic peroxides", ed. D. Swern Wiley-Interscience, New York, vol.1,Ch.IV, (1970).
  92. P.D. Bartlett and J.D. Cotman, J. Am. Chem. Soc., 71,1419 (1949).
  93. P. Bhargava and K. S. Gupta, Indian J. Chem., 32A, 201 (1993).
  94. W. M. Latimer, "The Oxidation States of the Elements and their Potentials in Aqueous Solution", Prentice Hall, New York, p.78 (1952).
  95. W.V. Steela and E.H. Applemen, J. Chem. Thermodyn., 14, 337 (1982).
  96. D.H. Fortnum, C.J. Battaglia, S.R. Cohen and J.O. Edwards, J. Am. Chem. Soc., 82,778 (1960).
  97. R. Renganathan and P. Maruthamuthu, J. Chem. Soc., Perkin Trans. 2, 285 (1986).
  98. R. Renganathan and P. Maruthanmuthu, Int.J. Chem.Kinet., 18, 49 (1986).

Publication Details

Published in : Volume 4 | Issue 10 | September-October 2018
Date of Publication : 2018-10-30
License:  This work is licensed under a Creative Commons Attribution 4.0 International License.
Page(s) : 385-394
Manuscript Number : IJSRST1841095
Publisher : Technoscience Academy

Print ISSN : 2395-6011, Online ISSN : 2395-602X

Cite This Article :

K. RamKumar, S. Thanga Malathi, " Oxidation of Indole - 3 - Propionic Acid by Peroxodisulphate in T - Butanol - A Kinetic Study, International Journal of Scientific Research in Science and Technology(IJSRST), Print ISSN : 2395-6011, Online ISSN : 2395-602X, Volume 4, Issue 10, pp.385-394, September-October-2018. Available at doi : 10.32628/IJSRST1841095
Journal URL : http://ijsrst.com/IJSRST1841095

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