Ruthenium catalyzed oxidative conversion of isatins to anthranilic acids: Mechanistic study

AIChE Journal

Volumn 54, Issue 3, 2008, Pages 756-765

  Jagadeesh, R Y ^a   Puttaswamy, ^b   Vaz, Nirmala ^c   Made Gowda, N M ^d  

^a University of Florida ^*  (United States)

^b BANGALORE UNIVERSITY   (India)

^c Jyoti Nivas College   (India)

^d WESTERN ILLINOIS UNIVERSITY   (United States)

Author keywords

Acid medium; Bromamine T; Isatins; Oxidation kinetics; Ru(III) catalysis

Indexed keywords

ACID MEDIUM; BROMAMINE-T; ISATINS; OXIDATION-KINETICS; RU(III)-CATALYSIS;

NITROGEN COMPOUNDS; PARAMETER ESTIMATION; REACTION KINETICS; RUTHENIUM;

CATALYST ACTIVITY;

CATALYST ACTIVITY; NITROGEN COMPOUNDS; PARAMETER ESTIMATION; REACTION KINETICS; RUTHENIUM;

EID: 42149162829     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.11416     Document Type: Article

References (41)

1. Silva da JFM, Garden SJ, Pinto AC. The chemistry of isatins: a review from 1975-1999. J Braz Chem Soc. 2001;12:273-324 and references therein.
2. Puttaswamy, Jagadeesh RV. Mechanistic investigations of oxidation of isatins by sodium N-chlorobenzenesulfonamide in alkaline medium: a kinetic study. Centl Eur J Chem. 2005;3:482-501.
3. Bishop E, Jennings VJ. Titrimetric analysis with chloramine-T: the status of chloramine-T as a titrimetric reagent. Talanta. 1958;1:197-199.
4. Morris JC, Salazar JR, Winemann MA. Equilibrium studies on chloro compounds: the ionization constant of N-chloro-p-toluenesulfonamide. J Am Chem Soc. 1948;70:2036-2041.
5. Higuchi T, Hussain A. Mechanism of chlorination of cresol by chloramine-T, mediation by dichloramine-T. J Chem Soc B. 1967;549-552.
6. Campbell MM, Johnson G. Chloramine-T and related N-halogeno-ZVmetallo reagents. Chem Rev. 1978;78:65-79.
7. Banerji KK, Jayaram B, Mahadevappa DS. Mechanistic aspects of oxidation by N-metallo N-haloarylsulfonamides. J Sci Ind Res. 1987;46;65-76.
8. Puttaswamy, Anuradha TM, Ramachandrappa R, Gowda NMM. Oxidation of isoniazid by N-haloarenesulfonamidates in alkaline medium: a kinetic and mechanistic study, Int J Chem Kinet. 2000;32:221-230.
9. Bhat KR, Jyothi K, Thimme Gowda B. Mechanism of Ru(III) catalyzed Tl(III)oxidation of di- and tri-substituted phenols in aqueous acetic acid. A kinetic study. Oxidation Commun. 2002;25:117-124 and references therein.
10. 4. Oxidation Commun. 2001;24:558-562 and references therein.
11. Rangappa KS, Ramachandra H, Mahadevappa DS. Mechanistic studies of oxidation of diphenylmethanols by sodium N-chlorobenzenesulphonamide catalysed by ruthenium(III). J Phys Org Chem. 1997;10:159.
12. Kamble DL, Nadibewoor ST. Osmium(VIII)Zruthenium(III) catalysis of periodate oxidation of acetaldehyde in aqueous alkaline medium. J Phys Org Chem. 1998;11:171-176.
13. 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.
14. Puttaswamy, Jagadeesh RV, Nirmala Vaz, Radhakrishna A. Ru(III)catalyzed oxidation of some N-heterocycles by chloramine-T in hydrochloric acid medium: a kinetic and mechanistic study. J Mol Catal A: Chem. 2005;229:211-220.
15. Nair CGR, Kumari RL, Indrasenan P. Bromamine-T as a new oxidimetric titrant. Talanta. 1978;25:525-527.
16. Vogel AI. Text Book of Quantitative Inorganic Analysis, 4th ed. London: ELBS-Longman, 1978:427.
17. Ramachandrappa R, Puttaswamy, Mayanna SM, Gowda. NMM. Kinetics and mechanism of oxidation of aspirin by bromamine-T, N-bromosuccinamide and N-bromophthalimide. Int J Chem Kinet. 1998;30:407-414.
18. Akerloff G. Dielectric constants of some organic solvents-water mixture at various temperatures. J Am Chem Soc. 1932;54:4125.
19. Pryde BG, Soper FD. The direct interchange of chlorine in the interaction of p-toluenesulfonamide and N-chloroacetalinide. J Chem Soc 1931:1510-1512.
20. Morris JC, Salazar JA, Wineman MA. Equilibrium studies on chloro compounds. The ionization constant of N-chloro p-toluenesulfonamide. J Am Chem Soc. 1948;70:2036-2041.
21. Higuchi T, Ikeda K, Hussain A. Mechanism and thermodynamics of chlorine transfer among organochlorinating agents. II. Reversible disproportination of chloramine-T. J Chem Soc B. 1967:546-549.
22. Narayanan SS, Rao VRS. Chlorine isotopic exchange reaction between chloramine-T and chloride ion. Radiochim Acta. 1983; 32:211.
23. Subhashini M, Subramanian M, Rao VRS. Determination of the protonated constant of chloramine-B. Talanta. 1985;35:1082-1083.
24. +. J Am Chem Soc. 1958;80:2646.
25. +. J Am Chem Soc. 1960;82:4187.
26. Backhours JR, Doyer FD, Shales N. Chemistry of Ru(IV) potential of quadravalentZtrivalene Ru couple in HCl. Proc Roy Soc London. 1950;83:146-155.
27. Davfokratova T. Analytical Chemistry of Ruthenium. USSR: Academy of Sciences, 1963:54, 71, 97.
28. Griffith WP. The Chemistry of Rare Platinum Metals. New York: Inter Science, 1967:141.
29. Ananda S, Venkatesha BM, Mahadevappa DS, Gowda NMM. Ruthenium(III) catalyzed kinetics of chloroacetic acids oxidation by sodium iV-bromobenzenesulfonamide in hydrochloric acid medium, Int J Chem Kinet. 1993;25:755.
30. Puttaswamy, Ramachandrappa R, Ramalingaiah. Ruthenium(III) catalyzed oxidation of amides by sodium N-bromebenzenesulfonamide in hydrochloric acid: a kinetic and mechanistic study. Transition Met Chem. 1999;24:52-58.
31. Puttaswamy, Nirmala Vaz. Kinetics and mechanism of ruthenium(III) and osmium(VIII) catalyzed oxidation of dopamine with bromamine-B in acid and alkaline media. Stud Surf Sei Catal. 2001;133:535-540.
32. Puttaswamy, Nirmala Vaz. Ruthenium(III)- and osmium(VIII)- catalyzed oxidation of 2-thiouracil by bromamine-B in acid and alkaline media: a kinetic and mechanistic study. Transition Met Chem. 2003; 28:409-417.
33. Ardon M. Oxidation of ethanol by eerie Perchlorate. J Chem Soc. 1957;1811-1815.
34. Collins CJ, Bowman NS. Isotope Effects in Chemical Reactions. New York: Van Nostrand Reinhold, 1970:267.
35. Wiberg KB. The deuterium isotype effect. Chem Rev. 1955;55:713.
36. Wiberg KB. Physical Organic Chemistry. New York: Wiley, 1964.
37. Amis ES, Jaffe G. The derivation of a general kinetic equation for reaction between ions and dipolar molecules. J Chem Phys. 1942;10:598.
38. Laidler KJ. Chemical Kinetics. Mumbai: Tata McGrawHill, 1965:246.
39. Gilliom RD. Introduction to Physical Organic Chemistry. London: Addison-Wesley, 1970:264.
40. Exner O. Entropy-enthalpy compensation and anti-compensation: salvation and ligand binding. Chem Commun. 2000;1655-1656 and references therein.
41. Moelwyn-Hughes EA. Kinetics of Reaction in Solutions. London: Oxford University Press, 1947:297-299.