Homolytic Bond Dissociation Enthalpies of the C-H Bonds Adjacent to Radical Centers

Journal of Organic Chemistry

Volumn 63, Issue 6, 1998, Pages 1872-1877

  Zhang, Xian Man ^a,b  

^a WESLEYAN UNIVERSITY   (United States)

^b NANKAI UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001522025     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971768d     Document Type: Article

References (54)

1. Viehe, H. G.; Janousek, Z.; Merenyi, R. Eds. Substituent Effects in Radical Chemistry; D. Reidel Publishing Co.: Dordrecht, Holland, 1986; NATO ASI Series C, Vol. 189.
2. Davies, K. J. A. Oxidative Damage and Repair; Pergamon Press: New York, 1991.
3. Scott, G., Ed. Atmospheric Oxidation and Antioxidants; Elsevier: Amsterdam, 1993; Vols. I, II, and III.
4. (a) Bunnett, J. F. Acc. Chem. Res. 1978, 11, 413.
5. (b) Kornblum, K. Angew. Chem., Int. Ed. Engl. 1975, 14, 734.
6. (c) Ashby, E. C. Acc. Chem. Res. 1988, 21, 414.
7. (d) Eberson, L. Electron-Transfer Reactions in Organic Chemistry; Springer-Verlag: New York, 1987.
8. (e) Zhang, X.-M.; Yang, D.-L.; Liu, Y.-C. J. Org. Chem. 1993, 58, 224.
9. (a) Zhang, X.-M.; Cheng, J.-P. Trends in Organic Chemistry, in press,
10. (b) Bordwell, F. G.; Zhang, X.-M. Acc. Chem. Res. 1993, 26, 510.
11. (c) McMillen, D. F.; Golden, D. F. Annu. Rev. Phys. Chem. 1982, 33, 493.
12. (d) Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
13. (e) Wayner, D. D. M.; Parker, V. D. Acc. Chem. Res. 1993, 26, 287.
14. (a) Mahoney, L. R.; Ferris, F. C.; DaRooge, M. A. J. Am. Chem. Soc. 1969, 91, 3883.
15. (b) Liu, B.; Huan, Z.-W.; Cheng, J.-P. Acta Chim. Sin. 1997, 55, 123.
16. (c) Cheng, J.-P.; Zhao, Y.-Y.; Huan, Z.-W. Sci. China, B. 1995, 38, 1417.
17. (d) Zhao, Y.-Y.; Huan, Z.-W.; Cheng, J.-P. Chem. J. Chinese Univ. 1994, 15, 207.
18. (e) Cheng, J.-P.; Zhao, Y.-Y. Tetrahedron, 1993, 49, 5267.
19. (f) Cheng, J.-P.; Liu, B.; Lu, Y.; Mi, J.-L.; Huan, Z.-W. Chem. J. Chinese University 1997, 18, 1080.
20. (a) Ander, P.; Sonnessa, A. J. Principles of Chemistry; The Macmillan Co.: New York, 1965; pp 515-518.
21. (b) Zhang, X.-M.; Bordwell, F. G. J. Org. Chem. 1994, 59, 2809
22. (a) Koenig, T. In Free Radicals, Vol. I, Kochi, J. K. Ed. Wiley: New York, Chapter 3, 1973.
23. (b) Tsang, W. J. Am. Chem. Soc. 1985, 107, 2872.
24. (a) Guo, Y.; Grabowski, J. J. J. Am. Chem. Soc. 1991, 113, 5926.
25. (b) Stein, S. E.; Brown, R. L. J. Am. Chem. Soc. 1991, 113, 787.
26. (a) Ochterski, J. W.; Petersson, G. A.; Montgomery, J. A. Jr. J. Chem. Phys. 1996, 104, 2598.
27. (b) Ochterski, J. W.; Petersson, G. A.; Wiberg, K. B. J. Am. Chem. Soc. 1995, 117, 11299.
28. (c) Rablen, P. R; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 4648.
29. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Foresman, J. B.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Ayala, P. Y.; Wong, M. W.; Replogle, E. S.; Gomperts, R.; Andres, J. L.; Raghavachari, K.; Binkley, J. S.; Gonzalez, C.; Martin, R. L.; Fox, D. J.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Pople, J. A. Gaussian 92; Gaussian, Inc.; Pittsburgh, P. A, 1993.
30. Lide, D. R. CRC Handbook of Chemistry and Physics, 76th ed.; CRC Press: Boca Raton, 1995-1996; (a) p 5-23, (b) p 9-64.
31. Lide, D. R. CRC Handbook of Chemistry and Physics, 76th ed.; CRC Press: Boca Raton, 1995-1996; (a) p 5-23, (b) p 9-64.
32. Lide, D. R. CRC Handbook of Chemistry and Physics, 76th ed.; CRC Press: Boca Raton, 1995-1996; (a) p 5-23, (b) p 9-64.
33. Zhang, X.-M.; Bordwell, F. G. J. Org. Chem. 1992, 57, 4163.
34. Zhang, X.-M.; Bordwell, F. G. J. Am. Chem. Soc. 1992, 114, 9787.
35. Bordwell, F. G.; Zhang, X.-M.; Alnajjar, M. S. J. Am. Chem. Soc. 1992, 114, 7623.
36. (a) Mulliken, R. S.; Rieke, C. A.; Brown, W. G. J. Am. Chem. Soc. 1941, 63, 41.
37. (b) Deasy, C. L. Chem. Rev. 1945, 36, 145.
38. Reutov, D. A. Fundamentals of Theoretical Organic Chemistry; Translated by Katz, T. J.; Appleton-Century-Crofls: New York, 1969; p 173.
39. Simic, M. G.; Jovanovic, S. V.; Niki, E. Am. Chem. Soc. Symp. Ser. 1992, 500, 14-32.
40. Zhu, Q.; Zhang, X.-M.; Fry, A. J. Polym. Degrad. Stab. 1997, 57, 43 and references therein.
41. (a) Sawyer, D. T. J. Phys. Chem. 1989, 93, 7977.
42. (b) Merenyi, G.; Lind, J. J. Phys. Chem. 1990, 94, 5412.
43. (c) Howard, C. J. J. Am. Chem. Soc. 1980, 102, 6937.
44. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper & Row Publishers: New York, 1981; p 715.
45. (a) Glaser, R.; Choy, G. S.-C. J. Phys. Chem. 1994, 98, 11379.
46. (b) Wiberg, K. B.; Cheeseman, J. R.; Ochtersk, J. W.; Frisch, M. J. J. Am. Chem. Soc. 1995, 117, 6535.
47. (c) Mo, Y.; Lin, Z.; Wu, W.; Zhang, Q. J. Phy. Chem. 1996, 100, 6469.
48. Zhang, X,-M.; Zhu, Q. J. Org. Chem. 1997, 62, 5934-5938.
49. (b) Zhang, X.-M.; Chen, Q.; Mantzaris, J. Rubber Chem. Technol. in press.
50. Wade, L. G., Jr, Organic Chemistry, 2nd ed.; Prentice Hall, New Jersey, 1991; (a) p 630, (b) p 675.
51. Wade, L. G., Jr, Organic Chemistry, 2nd ed.; Prentice Hall, New Jersey, 1991; (a) p 630, (b) p 675.
52. Wade, L. G., Jr, Organic Chemistry, 2nd ed.; Prentice Hall, New Jersey, 1991; (a) p 630, (b) p 675.
53. (a) Korolev, V. A.; Nefedov, O. Adv. Phys. Org. Chem. 1995, 30, 36.
54. (b) Shepherd, R. A.; Doyle, T. J.; Graham, W. R. M. J. Chem. Phys. 1988, 89, 2738.