Effects of ascorbic acid on arenediazonium salts reactivity: Kinetics and mechanism of the reaction

Helvetica Chimica Acta

Volumn 84, Issue 3, 2001, Pages 632-648

  Costas Costas, Ugo ^a   Gonzalez Romero, Elisa ^a   Bravo Diaz, Carlos ^a  

^a UNIVERSITY OF VIGO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AGENTS; ETHERS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ORGANIC ACIDS; PH EFFECTS; PHENOLS; REACTION KINETICS; SPECTROPHOTOMETRY;

HETEROLYTIC PRODUCTS;

SALTS;

2 METHYLBENZENEDIAZONIUM TETRAFLUOROBORATE; 3 METHYLBENZENEDIAZONIUM TETRAFLUOROBORATE; 4 METHYLBENZENEDIAZONIUM TETRAFLUOROBORATE; 6 HYDROXY 2 NAPHTHALENESULFONIC ACID; ASCORBIC ACID; BENZENE DERIVATIVE; DIAZONIUM COMPOUND; ETHER DERIVATIVE; PHENOL DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM; SULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CONCENTRATION (PARAMETERS); DECOMPOSITION; ELECTROCHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PH; POLAROGRAPHY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0035051938     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20010321)84:3<632::AID-HLCA632>3.0.CO;2-0     Document Type: Article

References (53)

1. R. N. Loeppky, C. J. Michejda, 'Nitrosamines and Related N-Nitroso Compounds. Chemistry and Biochemistry', Vol. 553, American Chemical Society, Washington, 1994.
2. D. H. L. Williams, 'Nitrosation', Cambridge University Press, Oxford, 1988.
3. R. Preussmann, B. W. Stewart, 'N-Nitroso Carcinogens', Vol. 182, American Chemical Society, Washington, 1984.
4. K. J. Reszka, C. F. Chignell, J. Am. Chem. Soc. 1993, 115, 7752.
5. K. J. Reszka, C. F. Chignell, Chem.-Biol. Interact. 1995, 96, 223.
6. D. Klamann, in 'Methoden der Organischen Chemie', Vol. E16a, Part II, Houben-Weyl, Thieme, Stuttgart, 1990.
7. H. Hertel, in 'Ullmann's Encyclopedia of Industrial Chemistry', Vol. A8, VCH, Weinheim, 1987.
8. W. Herbs, K. Hunger, 'Industrial Organic Pigments: Production, Properties, Applications', VCH, 1993.
9. K. H. Saunders, R. L. M. Allen, 'Aromatic Diazo Compounds', Edward Arnold Publ. Ltd., Baltimore, 1985.
10. H. Zollinger, 'Diazo Chemistry I: Aromatic and Heteroaromatic Compounds', VCH, Weinheim, 1994.
11. R. Glaser, C. J. Horan, H. Zollinger, Angew. Chem., Int. Ed. 1997, 36, 2210.
12. A. Chauduri, J. A. Loughlin, L. S. Romsted, J. Yao, J. Am. Chem. Soc. 1993, 115, 8351.
13. A. Chauduri, L. S. Romsted, J. Yao, J. Am. Chem. Soc. 1993, 115, 8362.
14. I. M. Cuccovia, I. N. da Silva, H. Chaimovich, L. S. Romsted, Langmuir 1997, 13, 647.
15. I. M. Cuccovia, A. Agostinho-Neto, C. M. A. Wendel, H. Chaimovich, L. S. Romsted, Langmuir 1997, 13, 5032.
16. V. Soldi, J. Keiper, L. S. Romsted, I. M. Cuccovia, H. Chaimovich, Langmuir 2000, 16, 59.
17. L. S. Romsted, J. Zhang, L. Zhuang, J. Am. Chem. Soc. 1998, 120, 10046.
18. H. Zollinger, in 'The Chemistry of Triple Bonded Functional Groups', Eds. S. Patai, Z. Rappoport, J. Wiley & Sons, Ltd., Chichester, 1983.
19. J. P. Berth, J. Chem. Soc., Chem. Comm. 1989, 101.
20. D. P. Arya, P. M. Warner, D. J. Jebaratnam, Tetrahedron Lett. 1993, 34, 7823.
21. S. R. Tannenbaun, S. Tamir, T. D. Rojas-Walker, J. S. Wishnok, in 'Nitrosamines and Related N-Nitroso Compounds: Chemistry and Biochemistry', ACS Symposium Series, Vol. 553, Eds. R. N. Loeppky, C. J. Michedja, American Chemical Society, Washington DC 1994.
22. C. Galli, Chem. Rev. 1988, 88, 765.
23. O. Augusto, Free Rad. Biol. Med. 1993, 15, 329.
24. T. Kato, K. Kojima, K. Hiramoto, K. Kigugawa, Mutat. Res. 1992, 268, 105.
25. H. Ohshima, M. Friesen, C. Malaveille, I. Brouet, A. Hautefeulli, U. Bartsch, Food Chem. Toxicol. 1989, 27, 193.
26. B. Toth, J. Taylor, B. Matsson, P. Gannet, In Vivo 1989, 3, 17.
27. J. Riordan, B. L. Vallee, Meth. Enzymol. 1972, 25, 521.
28. 'Food Chemistry', Ed. O. R. Fennema, Marcel Dekker, New York 1985.
29. D. C. Havery, H. J. Chou, in 'Nitrosamines and Related N-Nitroso Compounds', ACS Symposium Series, Vol. 553, American Chemical Society, Washington, 1994.
30. P. Hanson, J. R. Jones, B. C. Gilbert, A. W. Timms, J. Chem. Soc., Perkin Trans. 2 1991, 1009.
31. M. P. Doyle, C. L. Nesloney, M. S. Shanklin, C. A. Marsh, K. C. Brown, J. Org. Chem. 1989, 54, 3785.
32. C. Galli, J. Chem. Soc., Perkin Trans. 2 1981, 1459.
33. C. Bravo-Diaz, E. Gonzalez-Romero, Anal. Chim. Acta 1999, 385, 373.
34. R. Pazo-LLorente, M. J. Rodriguez-Sarabia, E. Gonzalez-Romero, C. Bravo-Díaz, Int. J. Chem. Kinet. 1999, 31, 73.
35. C. Bravo-Díaz, M. J. Sarabia-Rodriguez, P. Barreiro-Sio, E. Gonzalez-Romero, Langmuir 1999, 15, 2823.
36. K. C. Brown, M. P. Doyle, J. Org. Chem. 1988, 53, 3255.
37. W. J. Boyle, T. Broxton, J. F. Bunnet, Chem. Commun. 1971, 1470.
38. J. F. Bunnet, H. Takayama, J. Org. Chem. 1968, 33, 1924.
39. A. F. Hegarty, in 'The Chemistry of Diazonium and Diazo Compounds', Ed. S. Patai, John Wiley & Sons, Ltd., Chichester, 1978.
40. H. Viertler, V. L. Pardini, R. R. Vargas, J. Wiley & Sons, N.Y. 1994.
41. C. Bravo-Díaz, M. E. Romero-Nieto, E. Gonzalez-Romero, Langmuir 2000, 16, 42.
42. A. J. Fry, in 'The Chemistry of Diazo and Diazonium Groups', Ed. S. Patai, John Wiley & Sons, Ltd., New York, 1978.
43. J. F. Bunnet, C. Yijima, J. Org. Chem. 1977, 42, 639.
44. T. J. Broxton, D. L. Roper, J. Org. Chem. 1976, 41, 2157.
45. M. P. Doyle, W. J. Bryker, J. Org. Chem. 1979, 44, 1572.
46. M. C. Garcia-Meijide, C. Bravo-Díaz, L. S. Romsted, Int. J. Chem. Kinet. 1998, 30, 31.
47. C. Bravo-Díaz, L. S. Romsted, M. Harbowy, M. E. Romero-Nieto, E. Gonzalez-Romero, J. Phys. Org. Chem. 1999, 12, 130.
48. C. Bravo-Díaz, M. Soengas-Fernandez, M. J. Rodriguez-Sarabia, E. Gonzalez-Romero, Langmuir 1998, 14, 5098.
49. M. E. Romero-Nieto, C. Bravo-Díaz, E. Gonzalez-Romero, Int. J. Chem. Kin. 2000, 32, 419.
50. R. M. Elofson, R. L. Edsberg, P. A. Mecherly, J. Electrochem. Soc. 1950, 97, 1950.
51. E. R. Atkinson, H. H. Warren, P. I. Abel, R. E. Wing, J. Am. Chem. Soc. 1950, 72, 915.
52. J. K. Kochi, J. Am. Chem. Soc. 1955, 77, 3208.
53. R. M. Elofson, F. F. Gadallah, J. Org. Chem. 1969, 34, 854.