Equilibrium acidities and homolytic bond dissociation energies of N-H and/or O-H bonds in N-phenylhydroxylamine and its derivatives

Journal of the American Chemical Society

Volumn 118, Issue 37, 1996, Pages 8777-8781

  Bordwell, Frederick G ^a   Liu, Wei Zhong ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYLAMINE;

ARTICLE; DRUG SYNTHESIS; MOLECULAR DYNAMICS; REACTION ANALYSIS;

EID: 0029833046     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja960152n     Document Type: Article

References (35)

1. Bordwell, F. G.; Fried, H. E.; Hughes, D. L.; Lynch, T.-Y.; Satish, A. V.; Whang, Y. E. J. Org. Chem. 1990, 55, 3330-3336.
2. (a) Sutherland, J. O. In Comprehensive Organic Chemistry; Barton, D., Ollis, W. P., Eds.; Pergamon Press: New York, 1979; Vol. 22, pp 185-218.
3. (b) Aurich, H. G. In The Chemistry of Amino, Nitroso and Nitro Compounds and Their Derivatives; Patai, S., Ed.; Wiley: New York, 1987; Part I, p 565.
4. (a) Bordwell, F. G.; Harrelson, J. A., Jr.: Lynch, T. Y. J. Org. Chem. 1990, 55, 3337-3341.
5. (b) Perkins, M. J.; Berti, C.; Brooks, D. J.; Grierson, L.; Grimes, J. A.-M.; Jenkins, T. C.; Smith, S. L. Pure Appl. Chem. 1990, 62, 195-200. and references cited therein.
6. (a) Matthews, W. S.; Bares, J. E.: Bartmess, J. E.; Bordwell, F. G.; Comforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCollum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006-7014.
7. (b) Bordwell, F. G.; McCallum, R. J.; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424-1427.
8. Olmstead, W. N.; Margolin, Z.; Bordwell, F. G. J. Org. Chem. 1980, 45, 3295-3299.
9. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165-195.
10. Bordwell, F. G.; Algrim, D. J. J. Am. Chem. Soc. 1988, 110, 2964-2968.
11. Hammett, L. P. Physical Organic Chemistry, 2nd ed.; McGraw-Hill: 1970; p 367.
12. (a) McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 483-532.
13. (b) Colussi, A. J.; Benson, S. W. Int. J. Chem. Kint. 1978, 10, 1139-1149.
14. (c) Jonsson, M.; Lind, J.; Eriksen, T. E.; Merenyi, G J. Am. Chem. Soc. 1994, 116, 1423.
15. (d) Denisov, E. T.; Khudyakov, I. V. Chem. Rev., 1987, 87, 1313.
16. Varlamov, V. J.; Denisov, E. T. Dokl. Akad. Nauk. USSR 1987, 293, 126-128.
17. -) values have been shown to give agreement with gas phase BDEs to ±3 kcal/mol, or better in most instances (the error between relative values in a series of closely related compounds will be much smaller, ca. ±0.5 kcal/mol experimental error).
18. (a) Venimadhavan, S.; Amarnath, K.; Harvey, N. G.; Arnett, E. M. J. Am. Chem. Soc. 1992, 114, 221.
19. (b) Bordwell, F. G.; Harrelson, J. A.; Lynch, T.-Y. J. Org. Chem. 1990, 55, 3337-3341.
20. (a) Bordwell, F. G.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 4858-4861.
21. (b) Bordwell, F. G.; Satish, A. V.; Zhang, S.; Zhang, X.-M. Pure Appl. Chem. 1995, 67, 735-740 and references cited therein.
22. (a) Kanabus-Kaminska, J. M.; Gilbert, B. C.; Griller, D. J. Am. Chem. Soc. 1989, 111, 3311.
23. (b) Wayner, D. D. M.; Lusztyk, E.; Page, D.; Ingold, K. U.; Mulder, P.; Laarhonen, L. J. J.; Aldrich, H. S., J. Am. Chem. Soc. 1995, 117, 8737-8744.
24. (a) Amett, E. M.; Jaris, L.; Mitchell, E. J.; Murty, T. S. S. R.; Gorrie, T. M.; Schleyer, P. v. R. J. Am. Chem. Soc. 1970, 92, 2365.
25. (b) Rosenberg, M. S.; Iogansen, A. V.; Mashkovsky, A. A.; Odinokov, S. E. Spectroscopy Lett. 1972, 5, 75-80.
26. Bordwell, F. G.; Zhang, X.-M.; Satish, A. V. J. Am. Chem. Soc. 1994, 116, 6605-6610.
27. Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363.
28. Rüchardt, C. Angew. Chem., Int. Ed. Engl. 1970, 9, 830-843 and Nicholas, A. M. P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850 have also called attention to the importance of changes in ground state energies in affecting bond dissociation energies.
29. Rüchardt, C. Angew. Chem., Int. Ed. Engl. 1970, 9, 830-843 and Nicholas, A. M. P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850 have also called attention to the importance of changes in ground state energies in affecting bond dissociation energies.
30. Sutherland, I. O. In Comprehensive Organic Chemistry Barton, D., Ollis, W. D., Eds.; Pergamon Press: 1979; Vol. 2, pp 185-218.
31. Brink, C. P.; Crumbliss, A. L. J. Org. Chem. 1982, 47, 1171.
32. Peltier, D.; Gueguen, M. J. Bull. Soc. Chim. Fran. 1969, 264.
33. Utzinger, G. E. Liebigs Ann. Chem. 1944, 556, 50.
34. Perronnet, J.; Girrault, P.; Demoute, J.-P. J. Heterocyd. Chem. 1980, 17, 727.
35. Ayyanger, N. R. Brahme, K. C.; Kalkote, U. R.; Srinivasan, K. V. Synthesis 1984, 938.