N-nitrosation of amines by NO2 and NO: A theoretical study

Journal of Physical Chemistry A

Volumn 111, Issue 11, 2007, Pages 2200-2205

  Zhao, Yi Lei ^a,b,e   Garrison, Stephen L ^a,b,e   Gonzalez, Carlos ^a   Thweatt, William David ^b,c,e   Marquez, Manuel ^a,c,d  

^a NATIONAL INSTITUTE OF STANDARDS AND TECHNOLOGY   (United States)

^b Philip Morris USA   (United States)

^c Philip Morris USA Research Center   (United States)

^d Arizona State University   (United States)

^e Philip Morris Interdisciplinary Network of Emerging Science and Technology (INEST)   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINYL RADICAL; FREE RADICAL MECHANISM; GAS-PHASE NITROSATION; HIGH-LEVEL CALCULATIONS;

AMINES; COMPLEXATION; ELECTRONIC STRUCTURE; HYDROGEN BONDS; REACTION KINETICS; SUBSTITUTION REACTIONS;

NITROGEN COMPOUNDS;

AMINE; HETEROCYCLIC COMPOUND; NITRIC OXIDE; NITROGEN DIOXIDE; NITROSO DERIVATIVE; PYRROLE DERIVATIVE; PYRROLIDINE; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; ENTROPY; HYDROGEN BOND; NITROSATION;

AMINES; ENTROPY; HETEROCYCLIC COMPOUNDS; HYDROGEN BONDING; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NITRIC OXIDE; NITROGEN DIOXIDE; NITROSATION; NITROSO COMPOUNDS; PYRROLES; PYRROLIDINES;

EID: 34047217865     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp0677703     Document Type: Article

References (35)

1. Magee, P. N.; Barnes, J. M. Br. J. Cancer 1956, 10, 114-122.
2. Scientific and Technical Assessment Report on Nitrosamines; EPA-600/6-77-001; U.S. Environmental Protection Agency: Research Triangle Park, NC, 1977.
3. Ichinose, T.; Fujii, K.; Sagai, M. Toxicology 1991, 67, 211-225.
4. Izquierdo-Pulido, M.; Barbour, J. F.; Scanlan, R. A. Food Chem. Toxicol. 1996, 34, 297-299.
5. Lijinsky, W. Mutat. Res.-Genetic Toxicol. Environ. Mutagen. 1999, 443, 129-138.
6. Spiegelhalder, B.; Preussmann, R. Carcinogenesis 1983, 4, 1147-1152.
7. Mitch, W. A.; Sharp, J. O.; Trussell, R. R.; Valentine, R. L.; Alvarez-Cohen, L.; Sedlak, D. L. Environ. Eng. Sci. 2003, 20, 389-404.
8. Challis, B. C.; Shuker, D. E. G.; Fine, D. H.; Goff, E. U.; Hoffman, G. A. Iarc Publ. 1982, 41, 11-20.
9. Mirvish, S. S.; Sams, J. P.; Panigot, M.; Babcook, D. M. Proc. Am. Assoc. Cancer Res. 1985, 26, 114-114.
10. Williams, D. L. H. Nitrosation; Cambridge University Press: New York, 1988; p 214.
11. Zolfigol, M. A.; Zebarjadian, M. H.; Chehardoli, G.; Keypour, H.; Salehzadeh, S.; Shamsipur, M. J. Org. Chem. 2001, 66, 3619-3620.
12. Shapley, D. Science 1975, 191, 268-270.
13. Herrmann, J.; Schuster, R. H. Kautsch. Gummi Kunstst. 1993, 46, 563-567.
14. Schuster, R. H.; Wunsch, G.; Blume, A. Kautsch. Gummi Kunstst. 1994, 47, 651.
15. Blume, A.; Wunsch, G.; Schuster, R. H. Kautsch. Gummi Kunstst. 1996, 49, 683-691.
16. Diaf, A.; Beckman, E. J. React. Polym. 1995, 25, 89-96.
17. Lui, H. L.; Conboy, J. J.; Hotchkiss, J. H. J. Agric. Food Chem. 1988, 36, 984-987.
18. Tozawa, H.; Kawabata, T. Bull. Jpn. Soc. Sci. Fish. 1986, 52, 1969-1974.
19. Tozawa, H.; Kawabata, T. Nippon Suisan Gakkaishi 1987, 53, 2209-2216.
20. Tozawa, H.; Kawabata, T. Nippon Suisan Gakkaishi 1987, 53, 2259-2262.
21. Tozawa, H.; Kawabata, T. Nippon Suisan Gakkaishi 1987, 53, 1449-1456.
22. Mirvish, S. S.; Ramm, M. D.; Sams, J. P.; Babcook, D. M. Cancer Res. 1988, 48, 1095-1099.
23. Skreiberg, O.; Kilpinen, P.; Glarborg, P. Combust. Flame 2004, 136, 501-518.
24. Perry, R. A.; Siebers, D. L. Nature 1986, 324, 657-658.
25. Mebel, A. M.; Diau, E. W. G.; Lin, M. C.; Morokuma, K. J. Phys. Chem. 1996. 100, 7517-7525.
26. Mebel, A. M.; Lin, M. C. Int. Rev. Phys. Chem. 1997, 16, 249-266.
27. Roose, T. R.; Hanson, R. K.; Kruger, C. H. Proc. Int. Symp. Shock Tubes Waves 1978. 11, 245.
28. Zhao, Y. L.; Houk, K. N.; Olson, L. P. J. Phys. Chem. A 2004, 108, 5864-5871.
29. Masuda, M.; Mower, H. F.; Pignatelli, B.; Celan, I.; Friesen, M. D.; Nishino, H.; Ohshima, H. Chem. Res. Toxicol. 2000, 13, 301-308.
30. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
31. (a) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji. H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Kiene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Chailacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03. revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
32. (b) Certain commercial materials and equipment are identified in this paper in order to specify procedures completely. In no case does such identification imply recommendation or endorsement by the National Institute of Standards and Technology, nor does it imply that the material or equipment identified is necessarily the best available for the purpose.
33. (a) Montgomery, J. A.; Frisch, M. J.; Ochterski, J. W.; Petersson, G. A. J. Chem. Phys. 1999, 110, 2822-2827.
34. (b) See Gaussian thermochemistry white papers and technical notes, http://www. gaussian.com/g-whitepap/thermo.htm.
35. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. J. Comput. Chem. 2003, 24, 669-681.