Nonclassical aryl radicals: Intermediates or transition states for the hydrogen shift reactions?

Journal of Organic Chemistry

Volumn 61, Issue 12, 1996, Pages 4111-4114

  Cioslowski, Jerzy ^a   Liu, Guanghua ^a   Moncrieff, David ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000093974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960150l     Document Type: Article

References (33)

1. Nonhebel, D. C.; Walton, J. C. Free Radical Chemistry; Cambridge University Press: Cambridge, England, 1974; pp 417-469.
2. Porter, G.; Ward, B. Proc. R. Soc. London A 1965, 287, 457. Scaiano, J. C.; Steward, L. C. J. Am. Chem. Soc. 1983, 105, 3609 and references cited therein. Sharma, R. K.; Kharasch, N. Angew. Chem., Int. Ed. Engl. 1968, 7, 36 and references cited therein.
3. Porter, G.; Ward, B. Proc. R. Soc. London A 1965, 287, 457. Scaiano, J. C.; Steward, L. C. J. Am. Chem. Soc. 1983, 105, 3609 and references cited therein. Sharma, R. K.; Kharasch, N. Angew. Chem., Int. Ed. Engl. 1968, 7, 36 and references cited therein.
4. Porter, G.; Ward, B. Proc. R. Soc. London A 1965, 287, 457. Scaiano, J. C.; Steward, L. C. J. Am. Chem. Soc. 1983, 105, 3609 and references cited therein. Sharma, R. K.; Kharasch, N. Angew. Chem., Int. Ed. Engl. 1968, 7, 36 and references cited therein.
5. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
6. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
7. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
8. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
9. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
10. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
11. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
12. Wornat, M. J.; Sarofim, A. F.; Lafleur, A. L. The Pyrolysis of Anthracene as a Model Coal-Derived Aromatic Compound. In Twenty-Four Symposium (International) on Combustion; The Combustion Institute: Pittsburgh, 1992; p 955. Wornat, M. J.; Lafleur, A. L.; Sarofim, A. F. Polycyclic Aromat. Compd. 1993, 3, 149. Badger, G. M.; Spotswood, T. M. J. Chem. Soc. 1960, 4420. Badger, G. M.; Novotny, J. J. Chem. Soc. 1961, 3400. Badger, G. M.; Kimber, R. W. L. J. Chem. Soc. 1961, 3407. Badger, G. M.; Jolad, S. D.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 771. Badger, G. M.; Kimber, R. W. L.; Novotny, J. Aust. J. Chem. 1964, 17, 778. Badger, G. M.; Donnelly, J. K.; Spotswood, T. M. Aust. J. Chem. 1964, 17, 1138, 1147.
13. Sarofim, A. F.; Longwell, J. P.; Wornat, M. J.; Mukherjee, J. The Role of Biaryl Reactions in the PAH and Soot Formation, Springer Ser. Chem. Phys. 59; Springer-Verlag: Berlin, 1994; p 485.
14. Kasai, P. H.; Clark, P. A.; Whipple, E. B. J. Am. Chem. Soc. 1970, 92, 2640.
15. Chen, R. H.; Kafafi, S. A.; Stein, S. E. J. Am. Chem. Soc. 1989, 111, 1418.
16. Cioslowski, J.; Liu, G.; Martinov, M.; Piskorz, P.; Moncrieff, D. J. Am. Chem. Soc. In press.
17. Johnson, R. P. J. Org. Chem. 1984, 49, 4857.
18. Gill, P. M. W.; Johnson, B. G.; Pople, J. A.; Frisch, M. J. Int. J. Quant. Chem. 1992, S26, 319.
19. Hameka, H. F. J. Org. Chem. 1987, 52, 5025. Pacansky, J.; Liu, B.; DeFrees, D. J. Org. Chem. 1986, 51, 3720.
20. Hameka, H. F. J. Org. Chem. 1987, 52, 5025. Pacansky, J.; Liu, B.; DeFrees, D. J. Org. Chem. 1986, 51, 3720.
21. Berkowitz, J.; Ellison, G. B.; Gutman, D. J. Phys. Chem. 1994, 98, 2744.
22. This deviation from the experimental value is somewhat smaller than the mean absolute deviation of 5.6 kcal/mol observed in a series of BLYP/6-31G* calculations of atomization energies, see: Johnson, B. G.; Gill, P. M. W.; Pople, J. A. J. Chem. Phys. 1993, 98, 5612.
23. McMurry, J. E.; Lectka, T. Acc. Chem. Res. 1992, 25, 47.
24. Cioslowski, J. J. Am. Chem. Soc. 1993, 115, 5177.
25. GAUSSIAN 92/DFT, Revision G.3; Frisch, M. J., Trucks, G. W., Schlegel, H. B., Gill, P. M. W., Johnson, B. G., Wong, M. W., Foresman, J. B., Robb, M. A., Head-Gordon, M., 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. J. P., Pople, J. A.; Gaussian, Inc.: Pittsburgh, PA, 1993.
26. Cioslowski, J.; Stefanov, B. B. Mol. Phys. 1995, 84, 707. Stefanov, B. B.; Cioslowski, J. J. Comput. Chem. 1995, 16, 1394. Cioslowski, J.; Nanayakkara, A.; Challacombe, M. Chem. Phys. Lett. 1993, 203, 137.
27. Cioslowski, J.; Stefanov, B. B. Mol. Phys. 1995, 84, 707. Stefanov, B. B.; Cioslowski, J. J. Comput. Chem. 1995, 16, 1394. Cioslowski, J.; Nanayakkara, A.; Challacombe, M. Chem. Phys. Lett. 1993, 203, 137.
28. Cioslowski, J.; Stefanov, B. B. Mol. Phys. 1995, 84, 707. Stefanov, B. B.; Cioslowski, J. J. Comput. Chem. 1995, 16, 1394. Cioslowski, J.; Nanayakkara, A.; Challacombe, M. Chem. Phys. Lett. 1993, 203, 137.
29. Bader, R. F. W. Atoms in Molecules: A Quantum Theory; Clarendon Press: Oxford, 1990.
30. Cioslowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1992, 114, 4382.
31. Cioslowski, J. J. Math. Chem. 1991, 8, 169. Cioslowaki, J. Int. J. Quant. Chem. 1990, S24, 15.
32. Cioslowski, J. J. Math. Chem. 1991, 8, 169. Cioslowaki, J. Int. J. Quant. Chem. 1990, S24, 15.
33. Cioslowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1991, 113, 4142.