Nitro ⇌ aci-Nitro Tautomerism

Journal of the American Chemical Society

Volumn 115, Issue 6, 1993, Pages 2348-2351

  Lammertsma, Koop ^a   Prasad, Bharatam V ^a  

^a UNIVERSITY OF ALABAMA AT BIRMINGHAM   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001146205     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00059a032     Document Type: Article

References (75)

1. Nielson, A. T. In The Chemistry of the Nitro and Nitroso Groups; Feuer, H., Ed.; Interscience: New York, 1969; Part 1, p 349.
2. Noland, W. E. Chem. Rev. 1955, 55, 137.
3. The Chemistry of Amine, Nitroso, and Nitro Compounds and Their Derivatives; Patai, S., Ed.; Wiley: New York, 1982: Morrison, H. A., p 165; Chow, Y. L., p 181; Batt, L., p 417.
4. International Agency for Research on Cancer in Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man; WHO: Lyon, 1982; Vol. 29, p 331.
5. The Chemistry of Amine, Nitroso, and Nitro Compounds and Their Derivatives; Patai, S., Ed.; Wiley: New York, 1982: Schwarz, H., Levsen, K., p 85.
6. The Chemistry of Amine, Nitroso, and Nitro Compounds and Their Derivatives Fry, A. J., p 319.
7. Bernasconi, C. F.; Zitomer, J. L.; Schuck, D. F. J. Org. Chem. 1992, 57, 1132.
8. Miyashita, M.; Awen, B. Z. E.; Yoshikoshi, A. Tetrahedron 1990, 7569.
9. Shaw, A. J.; Gescher, A. J. Chromatog. 1990, 505, 402.
10. Herman, L. W.; ApSimon, J. W. Tetrahedron Lett. 1984, 25, 1423.
11. Veltwisch, D.; Asmus, K.-D. J. Chem. Soc., Perkin Trans. 2 1982, 1143.
12. Sroková, I.; Vetešník, P.; Jurášek, A.; Kováč, J. Collect. Czech. Chem. Commun. 1981, 46, 3122.
13. McKillop, A.; Kobylechi, R. J. Tetrahedron 1974, 30, 1365.
14. More O'Ferrall, R. A.; Quirke, A. P. Tetrahedron Lett. 1989, 30, 4885.
15. Chattopadhyay, S. K.; Craig, B. B. J. Phys. Chem. 1987, 91, 323.
16. Meese, C. O.; Güsten, H. Z. Naturforsch. 1986, 41b, 265.
17. Terrier, F.; Ah-Kow, G.; Chatrousse, A.-P. J. Org. Chem. 1985, 50, 4583.
18. Grant, R. D.; Pinhey, J. T.; Rizzardo, E.; Smith, G. C. Aust. J. Chem. 1985, 38, 1505.
19. Pollet, P. L.; Perzanowski, H. P.; Gelin, S. Spectrochim. Acta 1984, 40A, 1007.
20. Dopp, D. O. Top. Curr. Chem. 1978, 55, 49.
21. Yip, R. W.; Wen, Y. X.; Gravel, D.; Giasson, R.; Sharma, D. K. J. Phys. Chem. 1991, 95, 6078.
22. Yip, R. W.; Sharma, D. K.; Giasson, R.; Gravel, D. J. Phys. Chem. 1984, 88, 5770.
23. Politzer, P.; Seminario, J. M.; Bolduc, P. R. Chem. Phys. Lett. 1989, 158, 463.
24. Cox, J. R.; Hillier, I. H. Chem. Phys. 1988, 124, 39.
25. Turner, A. G. J. Phys. Chem. 1986, 90, 6000.
26. Ritchie, J. P. J. Org. Chem. 1989, 54, 3553.
27. Egsgaard, H.; Carlsen, L.; Florêncio, H.; Drewello, T.; Schwarz, H. Ber. Bunsenges. Phys. Chem. 1989, 93, 76.
28. Egsgaard, H.; Carlsen, L.; Elbel, S. Ber. Bunsenges. Phys. Chem. 1986, 90, 369.
29. McKee, M. L. J. Phys. Chem. 1989, 93, 7365.
30. McKee, M. L. Chem. Phys. Lett. 1989, 164, 520.
31. McKee, M. L. J. Phys. Chem. 1986, 90, 2335.
32. Wodtke, A. M.; Hintsa, E. J.; Lee, Y. T. J. Chem. Phys. 1986, 84, 1044.
33. Wodtke, A. M.; Hintsa, E. J.; Lee, Y. T. J. Phys. Chem. 1986, 90, 3549.
34. Dewar, M. J. S.; Ritchie, J. P.; Alster, J. J. Org. Chem. 1985, 50, 1031.
35. Kaufman, J. J.; Hariharan, P. C.; Chabalowski, C.; Hotokka, M. Int. J. Quantum Chem., Quantum Chem. Symp. 1985, 19, 221.
36. Mijoule, C.; Odiot, S.; Fliszar, S.; Schnur, J. M. THEOCHEM 1987, 149, 311.
37. Kleier, D. A.; Lipton, M. A. THEOCHEM 1984, 109, 39.
38. Marynick, D. S.; Ray, A. K.; Fry, J. L.; Kleier, D. A. THEOCHEM 1984, 108, 45.
39. McKee, M. L. J. Am. Chem. Soc. 1986, 108, 5784.
40. Head-Gordon, M.; Pople, J. A. Chem. Phys. Lett. 1990, 173, 585.
41. Wiberg, K. B.; Breneman, C. M.; LePage, T. J. J. Am. Chem. Soc. 1990, 112, 61.
42. Smith, B. J.; Nguyen, M. T.; Bouma, W. J.; Radom, L. J. Am. Chem. Soc. 1991, 113, 6452.
43. Apeloig, Y.; Arad, D.; Rappoport, Z. J. Am. Chem. Soc. 1990, 112, 9131.
44. Pople, J. A.; Head-Gordon, M.; Fox, D. J.; Raghavachari, K.; Curtiss, L. A. J. Chem. Phys. 1989, 90, 5622.
45. Curtiss, L. A.; Jones, C.; Trucks, G. W.; Raghavachari, K.; Pople, J. A. J. Chem. Phys. 1990, 93, 2537.
46. Hehre, W. J.; Radom, L.; Schleyer, P. v. R.; Pople, J. A. Ab Initio Molecular Orbital Theory, Wiley: New York, 1986.
47. GAUSSIAN 90, Revision I; Frisch, M. J.; Head-Gordon, M.; Trucks, G. W.; Foresman, J. B.; Schlegel, H. B.; Raghavachari, K.; Robb, M.; Binkley, J. S.; Gonzalez, C.; DeFrees, D. J.; Fox, D. J.; Whiteside, R. A.; Seeger, R.; Melius, C. F.; Baker, J.; Martin, R. L.; Kahn, L. R.; Stewart, J. J. P.; Topiol, S.; Pople, J. A., Gaussian, Inc.: Pittsburgh, PA, 1990.
48. DeFrees, D. J.; McLean, A. D. J. Chem. Phys. 1985, 82, 333.
49. Bader, R. F. W. Atoms in Molecules—A Quantum Theory, Oxford: London.
50. Bader, R. F. W. Acc. Chem. Res. 1985, 18, 9.
51. Bader, R. F. W.; Nguyen-Dang, T. T. Adv. Quantum Chem. 1981, 14, 63.
52. Bader, R. F. W.; Nguyen-Dang, T. T.; Tal, Y. Rep. Prog. Phys. 1981, 44, 893.
53. Cremer, D.; Kraka, E. Croat. Chim. Acta 1984, 57, 1259.
54. Ritchie, J. P. J. Am. Chem. Soc. 1989, 111, 2517.
55. Tannenbaum, E.; Johnson, R. D.; Myers, R. J.; Gwinn, W. D. J. Chem. Phys. 1954, 22, 949.
56. Tannenbaum, E.; Myers, R. J.; Gwinn, W. D. J. Chem. Phys. 1956, 25, 42.
57. Trevino, S. F.; Prince, E.; Hubbart, C. R. J. Chem. Phys. 1980, 73, 2996.
58. Jeffrey, G. A.; Ruble, J. R.; Wingert, L. M.; Yates, J. H.; McMullan, R. K. J. Am. Chem. Soc. 1985, 107, 6227.
59. Cox, A. P.; Waring, S. J. Chem. Soc., Faraday Trans. 2 1972, 1060.
60. Wiberg, K. B.; Hadad, C. M.; LePage, T. J.; Breneman, C. M.; Frisch, M. J. J. Phys. Chem. 1992, 96, 671.
61. Trinquecoste, C.; Rey-Lafon, M.; Forel, M.-T. Spectrochim. Acta 1974, 30A, 813.
62. McKee, M. L. J. Am. Chem. Soc. 1985, 107, 1900.
63. Pedley, J. B.; Naylor, R. D.; Kirby, S. P. Thermodynamical Data of Organic Compounds, 2nd ed.; Chapman: New York, 1986.
64. Chase, M. W., Jr.; Davies, C. A.; Downey, J. R., Jr.; Frurip, D. J.; McDonald, R. A.; Syverud, A. N. J. Phys. Chem. Ref. Data 1985, 14, Suppl 1.
65. Li, W.-K. Croat. Chem. Acta 1990, 63, 127.
66. Thomas, D. A.; Bloor, J. E.; Bartmess, J. E. J. Am. Soc. Mass Spectrom. 1990, I, 295.
67. Diel, B. N.; Hope, H. Inorg. Chem. 1986, 25, 4448.
68. Edgecombe, K. E.; Boyd, R. J. Can. J. Chem. 1983, 61, 45.
69. Clark, T.; Chandrasekhar, J.; Spitznagel, G. W.; Schleyer, P. v. R. J. Comput. Chem. 1983, 3, 294.
70. Murdoch, J. R.; Streitwieser, A., Jr.; Gabriel, S. J. Am. Chem. Soc. 1978, 100, 6338.
71. Murrell, J. N.; Vidal, B.; Guest, M, F. J. Chem. Soc., Faraday Trans. 2 1975, 1577.
72. Mezey, P. G.; Kresge, A. J.; Csizmadia, I. G. Can. J. Chem. 1976, 54, 2526.
73. Wiberg, K. B. J. Am. Chem. Soc. 1990, 112, 4177.
74. Gobbi, A.; MacDougall, P. J.; Frenking, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1001.
75. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. Gas-phase Ion and Neutral Thermochemistry: J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1.