On the solution chemistry of parent nitrenium ion NH2+: The role of the singlet and triplet states in its reactions with water, methanol, and hydrocarbons

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 5853-5857

  Srivastava, Sanjay ^a   Kercher, Michael ^a   Falvey, Daniel E ^a  

^a University of Maryland   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBON; METHANOL; NITRENIUM ION; NITROGEN; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; PHOTOLYSIS; REACTION ANALYSIS; SPECTROPHOTOMETRY;

EID: 0033529809     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990324+     Document Type: Article

References (45)

1. Abramovitch, R. A.; Jeyaraman, R. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic: Orlando, FL, 1984; pp 297-357.
2. Gassman, P. G. Acc. Chem. Res. 1970, 3, 26-33.
3. McClelland, R. A. Tetrahedron 1996, 52, 6823-6858.
4. Peyerimhoff, S. D.; Buenker, R. J. Chem. Phys. 1979, 42, 167-176.
5. Cramer, C. J.; Dulles, F. J.; Storer, J. W.; Worthington, S. E. Chem. Phys. Lett. 1994, 218, 387-394.
6. van-Huis, T. J.; Leininger, M. L.; Sherrill, C. D.; Schaefer, H. F., III. J. Comput. Chem. 1998, 63, 1107-1142.
7. Gibson, S. T.; Greene, J. P.; Berkowitz, J. J. Chem. Phys. 1985, 83, 4319-4328.
8. Falvey, D. E.; Cramer, C. J. Tetrahedron Lett. 1992, 33, 1705-1708.
9. Cramer, C. J.; Dulles, F. J.; Falvey, B. E. J. Am. Chem. Soc. 1994, 116, 9787-9788.
10. Ford, G. P.; Scribner, J. D. J. Am. Chem. Soc. 1981, 103, 4281-4291.
11. Humphreys, W. G.; Kadlubar, F. F.; Guengerich, F. P. Proc. Natl. Acad. Sci. U.S.A. 1992, 89, 8278-8282.
12. Kadlubar, F. F. In DNA Adducts Identification and Significance; Hemminki, K., Dipple, A., Shuker, D. E. G., Kadlubar, F. F., Segerbäck, D., Bartsch, H., Eds.; University Press: Oxford, U.K., 1994; pp 199-216.
13. Hoffman, G. R.; Fuchs, R. P. P. Chem. Res. Toxicol. 1997, 10, 347-359.
14. Novak, M.; Kahley, M. J.; Lin, J.; Kennedy, S. A.; Swanegan, L. A. J. Am. Chem. Soc. 1994, 116, 11626-11627.
15. Fishbein, J. C.; McClelland, R. A. J. Chem. Soc., Perkin Trans. 2 1995, 653-662.
16. Anderson, G. B.; Yang, L. L.-N.; Falvey, D. E. J. Am. Chem. Soc. 1993, 115, 7254-7262.
17. Scribner, J. D.; Naimy, N. K. Cancer Res. 1975, 35, 1416-1421.
18. Famulok, M.; Boche, G. Angew. Chem., Int. Ed. Engl. 1989, 28, 468-469.
19. Novak, M.; Kennedy, S. A. J. Am. Chem. Soc. 1995, 117, 574-575.
20. Cramer, C. J.; Truhlar, D. J.; Falvey, D. E. J. Am. Chem. Soc. 1997, 119, 12338-12339.
21. Hoffman, R. V.; Kumar, A.; Buntain, G. A. J. Am. Chem. Soc. 1985, 107, 4731-4736.
22. Gassman, P. G.; Cryberg, R. L. J. Am. Chem. Soc. 1969, 91, 5176-5177.
23. Takeuchi, H.; Hayakawa, S.; Tanahashi, T.; Kobayashi, A.; Adachi, T.; Higuchi, D. J. Chem. Soc., Perkin Trans. 2 1991, 847-855.
24. Takeuchi, H.; Higuchi, D.; Adachi, T. J. Chem. Soc., Perkin Trans. 2 1991, 1525-1529.
25. Kirmse, W. Carbene Chemistry; Academic: New York, 1971.
26. Kirmse, W.; Killian, J.; Steenken, S. J. Am. Chem. Soc. 1990, 112, 6399-6400.
27. Carbenes; Moss, R. A., Jones, M., Eds.; Wiley: New York, 1983.
28. When TFA was left out of the photolysis mixtures, only traces of products were detected. We assume that protonation of the toluidine derivatives is necessary to avoid photooxidation of these products and the initiation of radical chain reactions.
29. Snell, F. D.; Snell, C. T. Colorimetric Methods of Analysis; Van Nostrand: New York, 1936; Vol. 1, p 658.
30. Harris, D. C. Quantitative Chemical Analysis; Freeman: New York, 1991; p 539.
31. Takeuchi, H.; Watanabe, K. J. Phys. Org. Chem. 1998, 11, 478-484.
32. Bartlett, P. D.; Simons, D. M. J. Am. Chem. Soc. 1960, 82, 1753-1756.
33. Quinkert, G.; Opitz, K.; Wiersdorff, W. W.; Weinlich, J. Tetrahedron Lett. 1963, 1863-1868.
34. Robbins, W. K.; Eastman, R. H. J. Am. Chem. Soc. 1970, 92, 6076-6077.
35. Cristol, S. J.; Bindel, T. H. J. Org. Chem. 1980, 45, 951-954.
36. Meiss, T.; Miller, S. I. J. Am. Chem. Soc. 1972, 94, 1989-1996.
37. Olah, G.; Kobayashi, S.; Tashiro, M. J. Am. Chem. Soc. 1972, 94, 7448-7461.
38. White, E. H.; Darbeau, R. W.; Chen, Y.; Chen, S.; Chen, D. J. Org. Chem. 1996, 61, 7986-7987.
39. Siskos, M. G.; Karkadis, A. K.; Steenken, S.; Karakostas, N.; Garas, S. K. J. Org. Ckem. 1998, 63, 3251-3259.
40. Dix, E. J.; Goodman, J. L. J. Phys. Chem. 1994, 98, 12609-12612.
41. Toscano, J. P.; Platz, M. S.; Nikolaev, V.; Popic, V. J. Am. Chem. Soc. 1994, 116, 8146-8151.
42. Olson, D. R.; Platz, M. S. J. Phys. Org. Chem. 1996, 9, 759-769.
43. Day, R. A.; Underwood, A. L. Quantitative Analysis; 4th ed.; Prentice Hall: Englewood Cliffs, NJ, 1980; p 605.
44. Katriztky, A. R.; Lewis, J.; Nie, P.-L. J. Chem. Soc., Perkin Trans. 1 1979,
45. Katriztky, A. R.; Lewis, J.; Nie, P.-L. J. Chem. Soc., Perkin Trans. 1 1979, 446-450.