Formation and nucleophilic capture of N-nitrosiminium ions

Canadian Journal of Chemistry

Volumn 77, Issue 5-6, 1999, Pages 1148-1161

  Chahoua, Latifa ^a   Vigroux, Alain ^a   Chiang, Yvonne ^a   Fishbein, James C ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

Carbocations; Iminium ions; Nitrosiminium ions; Nucleophilicity; acetoxynitrosamines

Indexed keywords

IONIC STRENGTH; PHOTOLYSIS; RATE CONSTANTS; SOLVENTS;

AQUEOUS MEDIA; CARBOCATIONS; FORWARD REACTIONS; IMINIUM IONS; NITROSIMINIUM ION; NUCLEOPHILICITIES; REVERSE REACTIONS; SOLVOLYSES; STRUCTURE REACTIVITY; Α-ACETOXYNITROSAMINE;

POSITIVE IONS;

AZIDE; ESTER; IMINE; SOLVENT;

ARTICLE; CHEMICAL REACTION KINETICS; DEGRADATION; IONIC STRENGTH; PHOTOLYSIS; SOLVATION; STRUCTURE ACTIVITY RELATION; SYNTHESIS; THERMODYNAMICS;

EID: 0033306392     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v99-108     Document Type: Article

References (32)

1. P.D. Lawley. In Chemical carcinogens. ACS monograph 182. Edited by C.D. Searle. American Chemical Society, Washington, D.C. 1984.
2. W. Lijinsky. Chemistry and biology of N-nitroso compounds. Cambridge University Press, Cambridge. 1992.
3. J.E. Baldwin, A. Scott, S.E. Branz, S.R. Tannenbaum, and L. Green. J. Org. Chem. 43, 2427 (1978).
4. C. Revis, M. Rajamaki, and J.C. Fishbein. J. Org. Chem. 60 7733 (1995).
5. L. Chahoua, M. Mesic', A. Vigroux, and J.C. Fishbein. J. Org. Chem. 62, 2500 (1997); H. Cai and J.C. Fishbein. Tetrahedron, 10 671 (1997).
6. L. Chahoua, M. Mesic', A. Vigroux, and J.C. Fishbein. J. Org. Chem. 62, 2500 (1997); H. Cai and J.C. Fishbein. Tetrahedron, 10 671 (1997).
7. H. Cai and J.C. Fishbein. J. Am. Chem. Soc. In press.
8. M. Rajamaki, A. Vigroux, L. Chahoua, and J.C. Fishbein. J. Org. Chem. 60, 2324 (1995).
9. A. Vigroux, A.J. Kresge, and J.C. Fishbein. J. Am. Chem. Soc. 117, 4433 (1995).
10. P.G. Stecher (Editor). The Merck index. 8th ed. Merck & Co., Rahway, N.J. 1968.
11. M. Wiessler. Angew. Chem. Int. Ed. 13, 743 (1974).
12. J. Graymore. J. Chem. Soc. 1353 (1932).
13. J. Hovinen. J.I. Finneman, S.N. Satapathy, J. Ho, and J.C. Fishbein. J. Am. Chem. Soc. 114, 10321 (1992), and refs. within.
14. J.P. Richard, M.E. Rothenberg, and W.P. Jencks. J. Am. Chem. Soc. 106, 1361 (1984).
15. R.B. Dunlap, G.A. Ghanim, and E.H. Cordes. J. Phys. Chem. 73, 1898 (1970); RR. Young and W.P. Jencks. J. Am. Chem. Soc. 99, 8238 (1977).
16. R.B. Dunlap, G.A. Ghanim, and E.H. Cordes. J. Phys. Chem. 73, 1898 (1970); RR. Young and W.P. Jencks. J. Am. Chem. Soc. 99, 8238 (1977).
17. M. Wiessler, G. Rossnagel, and B. Rugewitz-Blackholm. N-Nitroso compounds: occurrence, biological effects and relevence to human cancer. Vol. 52. Edited by I.K. O'Neill, R.C. von Borstel, R.C. Miller, J. Long, and H. Bartsch. IARC Sci. Pub., Lyon. 1977. p. 465; N. Frank and M. Wiessler. Carcinogen, 7, 365 (1986).
18. M. Wiessler, G. Rossnagel, and B. Rugewitz-Blackholm. N-Nitroso compounds: occurrence, biological effects and relevence to human cancer. Vol. 52. Edited by I.K. O'Neill, R.C. von Borstel, R.C. Miller, J. Long, and H. Bartsch. IARC Sci. Pub., Lyon. 1977. p. 465; N. Frank and M. Wiessler. Carcinogen, 7, 365 (1986).
19. M. Mochizuki, T. Anjo, N. Sekiguchi, A. Ikarashi, A. Suzuki, Y. Wakabayashi, and M. Okada. Chem. Pharm. Bull. 34, 3956 (1986).
20. M. Wiessler. N-Nitrosamines. Edited by J.-P. Anselme. ACS, Washington, D.C. 1979. p. 57.
21. S.S. Hecht and C.B. Chen. J. Org. Chem. 44, 1563 (1979).
22. T.L. Amyes and J.P. Richard. J. Am. Chem. Soc. 113, 1867 (1991).
23. (a) C.F. Bernaconi. Tetrahedron, 41, 3219 (1985); J.P. Richard. Tetrahedron, 51, 1535 (1995);
24. (a) C.F. Bernaconi. Tetrahedron, 41, 3219 (1985); J.P. Richard. Tetrahedron, 51, 1535 (1995);
25. (b) J.P. Richard, T.L. Amyes, V. Jagannadham, Y.G. Lee, and D.J. Rice. J. Am. Chem. Soc. 117, 5198 (1995)
26. O. Exner. In Correlation analysis in chemistry, recent advances. Edited by N.B. Chapman and J. Shorter. Plenum, New York. 1978.
27. N.C. Deno and W.L. Evans. J. Am. Chem. Soc. 79, 5804 (1957).
28. R.A. McClelland, V.M. Kanagasabapathy, N.S. Banait, and S. Steenken. J. Am. Chem. Soc. 113, 1009 (1991).
29. J.P. Richard and W.P. Jencks. J. Am. Chem. Soc. 106, 1373 (1984).
30. B. Wilson and J.E. Bartmess. J. Am. Chem. Soc. 113, 1762 (1991).
31. R.A. McClelland, V.M. Kanagsabapathy, N.S. Banait, and S. Steenken. J. Am. Chem. Soc. 114, 1816 (1992).
32. M.L. Sinnott and W.P. Jencks. J. Am. Chem. Soc. 102, 2026 (1980).