Hydride Affinities of Organic Radicals in Solution. A Comparison of Free Radicals and Carbenium Ions as Hydride Ion Acceptors

Journal of the American Chemical Society

Volumn 115, Issue 12, 1993, Pages 5067-5072

  Handoo, Kishan L ^a   Cheng, Jin Pei ^b   Parker, Vernon D ^c  

^a UNIVERSITY OF KASHMIR   (India)

^b NANKAI UNIVERSITY   (China)

^c UTAH STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001700494     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00065a017     Document Type: Article

References (42)

1. (a) Nicholas, A. M. de P.; Arnold, D. R. Can. J. Chem. 1982, 60, 2165.
2. Okamoto, A.; Snow, M. S.; Arnold, D. R. Tetrahedron 1986, 22, 6175.
3. Camaioni, D. M. J. Am. Chem. Soc. 1990, 112, 9475.
4. Parker, V. D. Acta Chem. Scand. 1992, 46, 307.
5. Parker, V. D. Acta Chem. Scand. 1992, 46, 501.
6. Parker, V. D. Acta Chem. Scand. 1992, 46, 1133.
7. Cheng, J.-P.; Handoo, K. L.; Parker, V. D. J. Am. Chem. Soc. 1993, 115, 2655.
8. (a) Wolf, J. F.; Staley, R. H.; Koppel, I.; Taagepera, M.; McIver, R. T.; Beauchamp, J. L.; Taft, R. W. J. Am. Chem. Soc. 1977, 99, 5417.
9. b) Lossing, F. P.; Holmes, J. L. J. Am. Chem. Soc. 1984, 106, 6917.
10. c) Schultz, J. C.; Houle, F. A.; Beauchamp, J. I. J. Am. Chem. Soc. 1984, 106, 3917.
11. d) Karaman, R.; Huang, J.-T.L.; Fry, J. L. J. Org. Chem. 1991, 56, 188.
12. (a) Arnett, E. M.; Petro, S. C. J. Am. Chem. Soc. 1978, 100, 2563.
13. b) Arnett, E. M.; Petro, S. C. J. Am. Chem. Soc. 1978, 100, 5402, 5408.
14. c) Arnett, E. M.; Petro, S. C.; Schleyer, P. v. R. J. Am. Chem. Soc. 1979, 101, 522.
15. d) Arnett, E. M.; Pienta, N. J. J. Am. Chem. Soc. 1980, 102, 3329.
16. e) Arnett, E. M.; Hofelich, T. C. J. Am. Chem. Soc. 1983, 105, 2889.
17. f) Arnett, E. M.; Hofelich, T. C. J. Am. Chem. Soc. 1982, 104, 3522.
18. (a) Ostovic, D.; Lee, I.-S.H.; Roberts, R. M. G.; Kreevoy, M. M. J. Org. Chem. 1985, 50, 4206.
19. b) Kreevoy, M. M.; Kotchevar, A. T. J. Am. Chem. Soc. 1990, 112, 3579.
20. Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res., in press.
21. (a) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458.
22. b) Parker, V. D. J. Am. Chem. Soc. 1993, 115, 1201 (erratum).
23. Parker, V. D. Acta Chem. Scand. 1992, 46, 692.
24. Parker, V. D.; Handoo, K. L.; Roness, F.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 7493.
25. Bausch, M. J.; Guadalupe-Fasano, G.; Peterson, B. M. J. Am. Chem. Soc. 1991, 113, 8384.
26. Zhang, X.; Bordwell, F. G.; Bares, J. E.; Cheng, J.-P.; Petrie, B. C. J. Org. Chem., in press.
27. Sim, B. A.; Griller, D.; Wayner, D. D. M. J. Am. Chem. Soc. 1989, 111, 754.
28. Eberson, L. Electron Transfer Reactions in Organic Chemistry; Springer Verlag: Berlin, 1987; Chapter 4.
29. Parker, V. D.; Hammerich, O. Acta Chem. Scand. 1977, B31, 883.
30. Trasatti, S. Pure Appl. Chem. 1986, 58, 955.
31. Anne, A.; Moiroux, J. J. Org. Chem. 1990, 55, 4608.
32. Klippenstein, J.; Arya, P.; Wayner, D. D. M. J. Org. Chem. 1991, 56, 6736.
33. Mathews, W. S.; Bares, J. E.; Bartness, J. E.; Bordwell, F. G.; Cornforth, F. J.; Drucker, G. E.; Margolin, Z.; McCallum, R. J.; McCallum, G. J.; Vanier, N. R. J. Am. Chem. Soc. 1975, 97, 7006.
34. Reitstöen, B.; Parker, V. D. J. Am. Chem. Soc. 1991, 113, 6954.
35. Lasson, E.; Parker, V. D. Anal. Chem. 1990, 62, 412.
36. Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456.
37. Bares, J. E. Ph.D. Thesis. Northwestern University, Evanston, IL, 1976.
38. Bausch, M. J.; Gaudalupe-Fasano, C.; Koohang, A. J. Phys. Chem. 1991, 95, 3420.
39. McMillen, D. F.; Golden, D. M. Annu. Rev. Phys. Chem. 1982, 33, 493.
40. Nagaoka, T.; Berinstain, A. B.; Griller, D.; Wayner, D. D. M. J. Org. Chem. 1990, 55, 3707.
41. Griller, D.; Simoes, J. A. M.; Mulder, P.; Sim, B. A.; Wayner, D. D. M. J. Am. Chem. Soc. 1989, 111, 7872.
42. Kolthoff, I. M.; Chantooni, M. K., Jr.; Bhowmik, S. J. Am. Chem. Soc. 1968, 90, 23.