Mechanism of oxidation of the antituberculosis drug isoniazid by bromate in aqueous hydrochloric acid medium

Industrial and Engineering Chemistry Research

Volumn 51, Issue 14, 2012, Pages 5135-5140

  Yalgudre, Ramesh S ^a   Gokavi, Gavisiddappa S ^a  

^a SHIVAJI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACID MEDIUM; ACTIVE SPECIES; DIIMIDE; HYDROCHLORIC ACID MEDIUM; HYDROGEN IONS; ION-PAIR COMPLEXES; ISONICOTINIC ACID; MECHANISM OF OXIDATION; PROTONATED; PROTONATION EQUILIBRIA; PSEUDO-FIRST-ORDER; RATE OF REACTION;

CARBOXYLIC ACIDS; HYDROCHLORIC ACID; HYDROGEN; OXIDANTS; PROTONATION;

HYDRAZINE;

EID: 84859620675     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie203058s     Document Type: Article

References (21)

1. Amos, R. I. J.; Gourlay, B. S.; Schiesser, C. H.; Smith, J. A.; Yates, B. F. A mechanistic study on the oxidation of hydrazides: Application to the tuberculosis drug isoniazid Chem. Commun. 2008, 1695
2. Burner, U.; Obinger, C.; Paumann, M.; Furtmuller, P. G.; Kettle, A. J. Transient and Steady-State Kinetics of the Oxidation of Substituted Benzoic Acid Hydrazides by Myeloperoxidase J. Biol. Chem. 1999, 274, 9494
3. Kulkarni, R. M.; Bilehal, D. C.; Nandibewoor, S. T. Oxidation of Isoniazid by Quinolinium Dichromate in an Aqueous Acid Medium and Kinetic Determination of Isoniazid in Pure and Pharmaceutical Formulations Anal. Sci. 2004, 20, 743
4. Lurie, Ju. Handbook of Analytical Chemistry; MIR Publishers: Moscow, 1971; p 301.
5. Furniss, B. S.; Hannaford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5 th ed.; Longman Scientific & Technical: London, 1989; p 1061.
6. Baral, N.; Pati, N. C.; Nayak, P. L.; Dash, S. B. Aqueous polymerization of acrylonitrile initiated by potassium bromate-thioacetamide redox system J. Macromol. Sci.-Chem. 1982, A 18 (4) 545
7. Mahadevaiah; Demappa, T. Kinetic studies on free radical polymerization of acrylonitrile, initiated by chloramine-T/hydrogen peroxide redox system J. Appl. Polym. Sci. 2006, 102, 5877
8. Mohammad, A. Kinetic studies on the bromate ion oxidation of 12-tungstocobaltate(II) in aqueous acid Transition Met. Chem. 2003, 28, 345
9. Thomson, R. C. Kinetic study of the reduction of bromate ion by oxovanadium(IV) in perchlorate solution Inorg. Chem. 1971, 10, 1892
10. Wheate, N. J.; Vora, V.; Anthony, N. G.; McInnes, F. J. Host-guest complexes of the antituberculosis drugs pyrazinamide and isoniazid with cucurbit[7]uril J. Incl. Phenom. Macrocycl. Chem. 2010, 68, 359
11. Anoussakdise, G.; Ristos, M.; Uri, C. Halogen ring monosubstituted benzoic acid hydrazides as ligands II. Ultraviolet spectra and pK determination Can. J. Chem. 1973, 51, 811
12. Reddy, C. S.; Manjari, P. S. Kinetics and mechanism of acid bromate oxidation of substituted 4-oxo acids Indian J. Chem. 2010, 49A, 418
13. Cortes, C. E. S.; Faria, R. B. Revisiting the kinetics and mechanism of bromate-bromide reaction J. Braz. Chem. Soc. 2001, 12, 775
14. Grancicova, O. The effect of tetrabutylammonium ion on the uncatalyzed bromate oscillator React. Kinet. Catal. Lett. 2008, 94, 99
15. Nath, U.; Das, S. S.; Deb, D.; Das, P. J. Tetra- n -alkylammonium bromates-New and efficient reagents for deoximation New J. Chem. 2004, 28, 1423
16. Das, S. S.; Nath, U.; Deb, D.; Das, P. J. A convenient method for the oxidation of aromatic amines to nitro compounds using tetra- n- alkylammonium bromates Synth. Commun. 2004, 34, 2359
17. Tavakol, H. Kinetic and thermodynamic study of inter- and intramolecular proton transfer in N ′-acetyl formahydrazide tautomers Int. J. Quantum Chem. 2011, 111, 3717
18. Kulkarni, P. P.; Kadam, A. J.; Desai, U. V.; Mane, R. B.; Wadgaonkar, P. P. A simple and efficient oxidation of hydrazides to N, N ′- diacylhydrazines using oxone in an aqueous medium J. Chem. Res.(S) 2000, 184-185
19. Jadhav, V. K.; Wadgaonkar, P. P.; Salunkhe, M. M. Oxidation of hydrazides using sodium perborate: formation of N, N ′-diacylhydrazines J. Chin. Chem. Soc. 1998, 45, 831
20. Kadam, S. D.; Supale, A. R.; Gokavi, G. S. Kinetics and mechanism of oxidation of benzoic acid hydrazide by bromate catalyzed by anderson type hexamolybdochromate(III) in aqueous acidic medium Z. Phys. Chem. 2008, 222, 635
21. Amis, E. S. Solvent Effects on the Reaction and Mechanism; Academic Press: New York, 1966; p 183.