The decomposition of aliphatic N-nitro amines in aqueous sulfuric acid. Bisulfate as a nucleophile

Canadian Journal of Chemistry

Volumn 74, Issue 10, 1996, Pages 1774-1778

  Cox, Robin A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Acid catalyzed; Bisulfate; Excess acidity; Kinetics; N nitro amines; Nucleophiles

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; CORRELATION THEORY; DECOMPOSITION; ENTHALPY; PH EFFECTS; REACTION KINETICS; SOLUTIONS; SULFURIC ACID; THERMAL EFFECTS;

ALIPHATIC NITRO AMINES; BISULFATE ION; FREE CARBOCATIONS; NUCLEOPHILE; PROTONATED ACINITRO TAUTOMER;

NITROSAMINES;

EID: 0030261228     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/v96-197     Document Type: Article

References (30)

1. R.A. Cox. Acc. Chem. Res. 20, 27 (1987).
2. J.T. Edward. J. Chem. Educ. 64, 599 (1987).
3. R.P. Bell. The proton in chemistry. 2nd ed. Cornell University Press, Ithaca, N.Y. 1973. pp. 160-164.
4. C.H. Arrowsmith, A. Awwal, B.A. Euser, A.J. Kresge, P.P.T. Lau, D.P. Onwood, Y.C. Tang, and E.C. Young. J. Am. Chem. Soc. 113, 172 (1991); C.H. Arrowsmith, A.J. Kresge, and Y.C. Tang. J. Am. Chem. Soc. 113, 179 (1991).
5. C.H. Arrowsmith, A. Awwal, B.A. Euser, A.J. Kresge, P.P.T. Lau, D.P. Onwood, Y.C. Tang, and E.C. Young. J. Am. Chem. Soc. 113, 172 (1991); C.H. Arrowsmith, A.J. Kresge, and Y.C. Tang. J. Am. Chem. Soc. 113, 179 (1991).
6. P. Politzer, N. Sukumar, K. Jayasuriya, and S. Ranganathan. J. Am. Chem. Soc. 110, 3425 (1988); J. P. Ritchie. J. Am. Chem. Soc. 111, 2517 (1989).
7. P. Politzer, N. Sukumar, K. Jayasuriya, and S. Ranganathan. J. Am. Chem. Soc. 110, 3425 (1988); J. P. Ritchie. J. Am. Chem. Soc. 111, 2517 (1989).
8. R.A. Cox. Can. J. Chem. 74, 1779 (1996).
9. H.J. Shine, J. Zygmunt, M.L. Brownawell, and J. San Filippo. J. Am. Chem. Soc. 106, 3610 (1984), and references cited therein.
10. J. Barrott, I.N. Denton, and A.H. Lamberton. J. Chem. Soc. 1998 (1953).
11. E.N. Vorob'eva, L.L. Kuznetsov, and B.V. Gidaspov. Zh. Org. Khim. 19, 698 (1983); J. Org. Chem. USSR, 19, 615 (1983).
12. E.N. Vorob'eva, L.L. Kuznetsov, and B.V. Gidaspov. Zh. Org. Khim. 19, 698 (1983); J. Org. Chem. USSR, 19, 615 (1983).
13. A.A. Astrat'ev. E.N. Vorob'eva, L.L. Kuznetsov, and B.V. Gidaspov. Zh. Org. Khim. 15, 1136 (1979); J. Org. Chem. USSR, 15, 1015 (1979).
14. A.A. Astrat'ev. E.N. Vorob'eva, L.L. Kuznetsov, and B.V. Gidaspov. Zh. Org. Khim. 15, 1136 (1979); J. Org. Chem. USSR, 15, 1015 (1979).
15. A.A. Glukhov, L.L. Kuznetsov, and B.V. Gidaspov. Zh. Org. Khim. 19, 704 (1983); J. Org. Chem. USSR, 19, 620 (1983).
16. A.A. Glukhov, L.L. Kuznetsov, and B.V. Gidaspov. Zh. Org. Khim. 19, 704 (1983); J. Org. Chem. USSR, 19, 620 (1983).
17. R.A. Cox. J. Phys. Org. Chem. 4, 233 (1991).
18. R.A. Cox, I. Onyido, and E. Buncel. J. Am. Chem. Soc. 114, 1358 (1992).
19. R.A. Cox, D. Moore, and R.S. McDonald. Can. J. Chem. 72, 1910 (1994).
20. J.-P. Bégué, F. Benayoud, D. Bonnet-Delpon, A.D. Allen, R.A. Cox, and T.T. Tidwell. Gazz. Chim. Ital. 125, 399 (1995).
21. R.A. Cox and K. Yates. J. Am. Chem. Soc. 100, 3861 (1978).
22. R.A. Cox, M.F. Goldman, and K. Yates. Can. J. Chem. 57, 2960 (1979).
23. a prediction for organic acids and bases. Chapman and Hall, London. 1981. (a) pp. 109-126; (b) pp. 37-38.
24. A.J. Kresge. Acc. Chem. Res. 8, 354 (1975).
25. R.A. Cox and K. Yates. Can. J. Chem. 60, 3061 (1982).
26. R.A. Cox. J. Am. Chem. Soc. 96, 1059 (1974).
27. R.A. Cox and K. Yates. Can. J. Chem. 59, 2853 (1981).
28. H.-M. Xiao, Y.-M. Li, and Y.-F. Li. Huaxue Xuebao, 53, 438 (1995); Chem. Abstr. 123, 313171v (1995).
29. H.-M. Xiao, Y.-M. Li, and Y.-F. Li. Huaxue Xuebao, 53, 438 (1995); Chem. Abstr. 123, 313171v (1995).
30. R.A. Cox and K. Yates. J. Org. Chem. 51, 3619 (1986).