Effects of structure on the reactivity of α-hydroxydialkylnitrosamines in aqueous solutions

Journal of the American Chemical Society

Volumn 118, Issue 31, 1996, Pages 7412-7413

  Mesić, Milan ^a   Revis, Cynthia ^a   Fishbein, James C ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NITROSAMINE;

ARTICLE; CARCINOGENICITY; DRUG STABILITY;

EID: 0029740207     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961178h     Document Type: Article

References (20)

1. Warning! The α-hydroxydialkylnitrosamines and their α-hydroperoxy precursors are presumed carcinogens and must be handled accordingly.
2. Lawley, P. D. In Chemical Carcinogens; Searle, C. D., Ed.; ACS Monograph 182; American Chemical Society: Washington, DC, 1984.
3. Lijinsky. Chemistry and Biology of N-nitroso Compounds; Cambridge University Press: Cambridge, 1992.
4. Mochizuki, M.; Anjo, T.; Okada, M. Tetrahedron Lett. 1980, 21, 3693.
5. Okada, M.; Mochizuki, M.; Anjo, T.; Sone, T.; Wakabayashi, Y.; Suzuki, E. IARC Sci. Publ. 1980, 31, 71.
6. Mochizuki, M.; Anjo, T.; Takeda, K.; Suzuki, E.; Sekiguchi, N.; Huang, G. F.; Okada, M. IARC Sci. Publ. 1980, 31, 71.
7. Loeppky, R. N. IARC Sci. Publ. 1980, 31, 82.
8. 3) δ 2.83, (s, 3 H); 7.23, (s, 1 H); 7.34-7.50, (m, 5 H); 11.3 (br, 1 H).
9. In the case of 2d, the traditional arrangement of the two-syringe mixing aparatus was replaced by introducing the substrate solution in acetonitrile, initially protected from the reaction cell by a 10-20 μL bolus of dry acetonitrile, into the reaction cell supply line by means of a T-junction and an additional filling syringe that contained the substrate solution and that could be isolated from the flow system by a third valve. The collinear ends of the T-junction were attached to the reaction cell by means of a 120 μL loop and to one of the two mixing syringes containing freshly dried (from CaH) acetonitrile.
10. 0 that were within 7% of those obtained in experiments in which a 10-fold excess of aqueous buffer was used.
11. R.
12. a of ≃0.2 units is calculated from the value for the ionization of alcohol of ρ* = -1.42. Ballinger, P.; Long, F. A. J. Am. Chem. Soc. 1960, 82, 795.
13. Funderburk, L. H.; Aldwin, L.; Jencks, W. P. J. Am. Chem. Soc. 1978, 100, 5444.
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15. Greenzaid, P. J. Org. Chem. 1973, 38, 3164.
16. a was recalculated as in ref 15 above.
17. Green, L. R.; Hine, J. J. Org. Chem. 1974, 39, 3896.
18. Schlesinger, G., Miller, S. L. J. Am. Chem. Soc. 1973, 95, 3729.
19. Bell, R. P. Adv. Phys. Org. Chem. 1966, , 1.
20. McClelland, R. A.; Coe, M. J. Am. Chem. Soc. 1983, 105, 2718.