Homolytic Bond Dissociation Energies in Solution from Equilibrium Acidity and Electrochemical Data

Journal of the American Chemical Society

Volumn 110, Issue 4, 1988, Pages 1229-1231

  Bordwell, F G ^a   Cheng, Jin Pei ^a   Harrelson, John A ^a  

^a NORTHWESTERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROCHEMISTRY; ORGANIC COMPOUNDS; THERMODYNAMICS;

ETHYL PHENYLACETATE; FLUORENE; HOMOLYTIC BOND DISSOCIATION ENERGIES (BDE); INDENE; THIOPHENOL;

CHEMICAL REACTIONS;

EID: 0023962831     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00212a035     Document Type: Article

References (25)

1. Hine, J. Structural Effects on Equilibrium in Organic Chemistry; Wiley-Interscience: New York, 1975; Chapters 1 and 10. Lowry, T. H.; Richardson, K. S. Mechanism and Theory in Organic Chemistry, 2nd ed.; Harper and Row: New York, 1981.
2. Benson, S. W. J. Chem. Ed. 1965, 42, 502–518. (b) Benson, S. W. Thermochemical Kinetics; Wiley: New York, 1968. (c) Golden, D. M.; Benson, S. W. Chem. Rev. 1969, 69, 125–134. (d) McMillen, D. F.; Golden, D. M. Ann. Rev. Phys. Chem. 1982, 33, 493–532.
3. Bordwell, F. G.; Bausch, M. J. J. Am. Chem. Soc. 1986, 109, 1979–1985.
4. Nicholas, A. M. P.; Arnold, D. R. Can. J. Chem. 1982, 60, 2165–2179.
5. Bordwell, F. G.; Bausch, M. J. J. Am. Chem. Soc. 1986, 108, 2473–2474. (b) Bausch, M. J. Ph.D. Dissertation, Northwestern University, 1984. (c) Cheng (Cheng, J.-P. Ph.D. Dissertation, Northwestern University, 1987) has reported estimates of acidities for over 200 radical cations.
6. Olmstead, W. N.; Margolin, Z.; Bordwell, F. G. J. Org. Chem. 1980, 45, 3295–3299. Bordwell, F. G.; Branca, J. C.; Hughes, D. L.; Olmstead, W. N. J. Org. Chem. 1980, 45, 3305–3313. Bordwell, F. G.; McCallum, R. J.; Olmstead, W. N. J. Org. Chem. 1984, 49, 1424–1427.
7. Solubility Data Series: Hydrogen and Deuterium; Young, C. L., Ed.; Pergamon: Oxford, 1981; Vol. 5/6.
8. Kolthoff, I. M.; Chantooni, M. K., Jr. J. Phys. Chem. 1972, 76, 2024–2034. (b) Benoit, R. L.; Louis, C. In The Chemistry of Nonaqueous Solvents; Lagowski, J. J., Ed.; Academic Press: New York, 1978, Vol. V-A, Chapter 2.
9. McMillen, D. F.; Trevor, P. L.; Golden, D. M. J. Am. Chem. Soc. 1980, 102, 7400–7402.
10. Robaugh, D. A. Ph.D. Dissertation, West Virginia University, 1983.
11. Rossi, M. J.; McMillen, D. F.; Golden, D. M. J. Phys. Chem. 1984, 88, 5031–5039.
12. Stein, S. E. In New Approaches in Coal Chemistry; ACS Symposium Series 169; American Chemical Society: Washington, DC, 1981; pp 97–129.
13. Swarc, M. Proc. R. Soc. London, Ser. A. 1951, 207, 5–13.
14. Furugama, S.; Golden, D. M.; Benson, S. W. Int. J. Chem. Kinet. 1971, 3, 237–248.
15. Lossing, F. P.; Traeger, J. C. J. Am. Chem. Soc. 1975, 97, 1579–1580.
16. McMahon, T. B.; Kebarle, P. J. Am. Chem. Soc. 1976, 98, 3399–3406.
17. Kerr, J. A. Chem. Rev. 1966 66, 465–500.
18. Colussi, A. J.; Benson, S. W. Int. J. Chem. Kinet. 1977, 9, 295–306. Colussi, A. J.; Benson, S. W. J. Am. Chem. Soc. 1978, 10, 1139–1149.
19. DeFrees, D. J.; Mclver, R. T., Jr.; Hehre, J. J. Am. Chem. Soc. 1980, 102, 3334–3338.
20. Carson, A. S.; Fine, D. H.; Gray, P.; Laye, P. G. J. Chem. Soc. B 1971, 1611-1615.
21. Bartmess, J. E., private communication.
22. King, K. D.; Golden, D. M.; Benson, S. W. J. Am. Chem. Soc. 1970, 92, 5541–5546.
23. Holmes, J. L.; Lossing, F. P.; Terlouw, J. K. J. Am. Chem. Soc. 1986, 108, 1086–1087.
24. Jaun, B.; Schwartz, J.; Breslow, R. J. Am. Chem. Soc. 1978, 102, 5741–5748.
25. Wayner, D. D. M.; Griller, D. J. Am. Chem. Soc. 1985, 107, 7764–7765.