Oxidation of vanillin and related compounds by sodium N-chloro-p- toluenesulfonamide in acid medium: A kinetic and mechanistic approach

Synthesis and Reactivity in Inorganic, Metal-Organic and Nano-Metal Chemistry

Volumn 35, Issue 10, 2005, Pages 845-854

  Puttaswamy, ^a   Suresha, N ^a   Jagadeesh, R V ^a   Vaz, Nirmala ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

Acid medium; Chloramine T; Oxidation kinetics; Vanillin and related compounds

Indexed keywords

EID: 33645536360     PISSN: 15533174     EISSN: 15533182     Source Type: Journal    
DOI: 10.1080/15533170500360446     Document Type: Article

References (38)

1. Akerloff, G. Dielectric constants of some organic solvents-water mixture at various temperatures. J. Am. Chem. Soc. 1932, 54, 4125-4135.
2. Amis, E. S. Coulomb's law and the quantitative interpretation of reaction rates (II). J. Chem. Educ. 1953, 30, 351-355;
3. Rates mechanisms and solvent. Anal. Chem. 1955, 27, 1672-1679.
4. Solvent Effects on Reaction Rates and Mechanisms; Academic Press: New York, 1966.
5. Ananda, S.; Jagadeesha, M. B.; Puttaswamy; Venkatesha, B. M.; Vinod, T. K. Kinetic and mechanistic studies of some aliphatic amines' oxidation by sodium N-bromo-p-toluenesulfonamide in hydrochloric acid medium, Gowda, N. M. M. Int. J. Chem. Kinet. 2000, 32, 776-783.
6. Banerji, K. K.; Jayaram, B.; Mahadevappa, D. S. Mechanistic aspects of oxidation by N-metallo-N-haloarylsulfonamides. J. Sci. Ind. Res. 1987, 46, 65-76.
7. Berka, A.; Vulterin, T.; Zyka, J. Newer Redox Titrants; Pergamon: New York, 1965; p. 37.
8. Bishop, E.; Jennings, V. J. Titrimetric analysis with chloramine-T: The status of chloramine-T as a titrimetric reagent. Talanta 1958, 1, 197-199.
9. Bremner, D. H. Synthesis of α-aminoaldehydes from enamines. Review: Synth. Reagent. 1985, 6, 9.
10. Campbell, M. M.; Johnson, G. Chloramine-T and related N-halogeno-N-metallo reagents. Chem. Rev. 1978, 78, 65-79.
11. Collins, C. J.; Bowman, N. S. Isotope Effect in Chemical Reactions; Van-Nostrand-Reinhold: New York, 1970; p. 267.
12. Exner, O. Entropy-enthalpy compensation and anticompensation: salvation and ligand binding. Chem. Commun. 2000; 1655-1656 and references therein.
13. Entelis, S. G.; Tiger, R. P. Reaction Kinetics in the Liquid Phase; Wiley: New York, 1976.
14. Hardy, F. F.; Johnston, J. P. The interactions of N-bromo-N- sodiobenzesulfonamide (bromamine-B) with p-nitrophenoxide ion. J. Chem. Soc. Perkin Trans. II 1973, 742-750.
15. House, J. E. Principles of Chemical Kinetics; Wm.C. Brown Publishes: Boston, 1997.
16. Katgeri, S. N.; Mahadevappa, D. S.; Naid, H. M.K. A rapid method for the estimation of glutamic acid with chloramine-T. Talanta 1979, 26, 420-422.
17. Kirkwood, J. Theory of solutions of molecules containing widely separated charges with special application to zwitterions. J. Chem. Phys. 1934, 2, 351-358.
18. Kothari, C.; Pol, P.; Nandibewoor, S. T. Kinetics and mechanism of oxidation of vanillin by diperiodatenicklate(IV) in aqueous alkaline medium. Turk. J. Chem. 2002, 26, 229-236.
19. Laidler, K. J. Chemical Kinetics; Mc-Graw Hill: New York, 1965.
20. Liadler, K. J.; Landskroener, P. A. The influence of the solvent on reaction rates. Trans. Faraday Soc. 1956, 52, 200-210.
21. Meenakshisundaram, S.; Sockalingam, R. M. Os(VIII)-catalysed oxidation of sulfides by sodium salt of N-chlorobenzenesulfonamide. J. Mole. Catal-A: Chemical 2000, 760, 269-275.
22. Morris, J. C.; Salazar, J. A.; Wineman, M. A. Equilibrium studies on chloro compounds: the ionization constant of N-chloro-p-toluenesulfonamide. J. Am. Chem. Soc. 1948, 70, 2036-2041.
23. Murthy, A. R. V.; Rao, B. S. Proc. Indian. Acad. Sci. 1952, 35, 69-72.
24. Narayan, S. S.; Rao, V. R. S. Chlorine isotopic exchange reaction between chloramine-T and chloride ion. Radio Chem. Acta. 1983, 52, 211-212.
25. Pryde, B. G.; Soper, F. G. The halogenation of phenols. J. Chem. Soc. 1926, 1582;
26. The direct interchange of chlorine in the interaction of p-toluenesulphonamide and N-chloroacetamide, and Pryde, B. G.; Soper, F. G. J. Chem. Soc. ibid 1931 1514-1518.
27. Puttaswamy; Ramachandrappa, R. Ruthenium(III)-catalyzed oxidation of substituted ethanols by sodium N-bromo-p-toluenesulfonamide in hydrochloric acid medium. Transition Met. Chem. 1999, 24, 326-332.
28. Puttaswamy; Anuradha, T. M.; Ramachandrappa, R.; Gowda, N. M. M. Oxidation of isoniazide by N-haloarenesulfonamides in alkaline medium: A kinetic and mechanistic study. Int. J. Chem. Kinet. 2000, 52, 221-230.
29. Puttaswamy; Nirmala, Vaz. Kinetic analysis of oxidation of dipeptides by sodium N-bromobenzenesulfonamide in acid medium: a mechanistic approach. Bull. Chem. Soc. Jpn. 2003, 76, 73-80.
30. Puttaswamy; Jagadeesh, R. V.; Nirmala, Vaz; Radhakrishna, A. Ru(III)-catalysed oxidation of some N-heterocycles by chloramine-T in hydrochloric acid medium: A kinetic and mechanistic study. J. Mole. Catal. A: Chem. 2005, 229 (1-2), 211-220.
31. Rangappa, K. S.; Raghavendra, M. P.; Mahadevappa, D. S. Kinetics and mechanism of oxidation of uronic acids by sodium N-chloro-p-toluenesulfonamide in alkaline medium. J. Carbohydr. Chem. 1997, 26, 359-371.
32. Rangappa, K. S.; Raghavendra, M. P.; Mahadevappa, D. S.; Channegowda, D. Sodium N-chloro-benzenesulphonamide as a selective oxidant for the hexosamines in alkaline medium: A kinetic and mechanistic study. J. Org. Chem. 1998, 63, 531-536.
33. Saldanha, R. J. D.; Ananda, S.; Venkatesha, B. M.; Gowda, N. M. M. Oxidation of psychotropic drugs by chloaramine-T in acid medium: a kinetic study using spectrophotometry. J. Mole. Structr. 2002, 606, 147-154.
34. Subhashini, M.; Subramanian, M.; Rao, V. R. S. Determination of the protonated constant of chloramines-B. Talanta 1985, 32, 1082.
35. Stecher, P. G., (Eds). The Merck Index (An Encyclopedia of Chemical and Drugs), 8th ed.; Merck & Co. Inc.: Rahway, NJ, 1968; p. 1102.
36. Tanford, C.; Kirkwood, J. Theory of protein titration curves. I. General equations for impenetrable spheres. J. Am. Chem. Soc. 1957, 79, 5333-5339.
37. Wiberg, K. B. The Deuterium Isotope Effect. Chem. Rev. 1955, 55, 713,
38. Physical Organic Chemistry; Wiley New York, 1964.