Computational assessment of polar ground-state effects on the bond dissociation energies of benzylic and related bonds

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 8312-8314

  Nau, Werner M ^a  

^a UNIVERSITY OF BASEL   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001308886     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961301n     Document Type: Article

References (17)

1. Zavitsas, A. A.; Pinto, J. A. J. Am. Chem. Soc. 1972, 94, 7390.
2. Agirbas, H.; Jackson, R. A. J. Chem. Soc., Perkin Trans. 2 1983, 739.
3. Nicholas, A. M. DE P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1850.
4. Suryan, M. M.; Kafafi, S. A.; Stein, S. E. J. Am. Chem. Soc. 1989, 111, 4594.
5. Clark, K. B.; Wayner, D. D. M. J. Am. Chem. Soc. 1991, 113, 9363.
6. Bordwell, F. G.; Zhang, X.-M.; Satish, A. V.; Cheng, J.-P. J. Am. Chem. Soc. 1994, 116, 6605.
7. Nau, W. M.; Harrer, H. M.; Adam, W. J. Am. Chem. Soc. 1994, 116, 10972.
8. Wu, Y.-D.; Wong, C.-L.; Chan, K. W. K.; Ji, G.-Z.; Jiang, X.-K. J. Org. Chem. 1996, 61, 746.
9. Viehe, H. G.; Janousek, Z.; Merényi, R. Substituent Effects in Radical Chemistry; Reidel: Dordrecht, The Netherlands, 1986.
10. Rüchardt, C. Top. Curr. Chem. 1980, 88, 1.
11. Pauling, L. In The Nature of the Chemical Bond; Cornell University Press: Ithaca, NY, 1960.
12. Rüchardt, C.; Beckhaus, H.-D. Top. Curr. Chem. 1985, 130, 1.
13. Leroy, G.; Sana, M.; Wilante, C. THEOCHEM 1990, 205, 97.
14. Nicholas, A. M. DE P.; Arnold, D. R. Can. J. Chem. 1984, 62, 1860.
15. Wayner, D. D. M.; Sim, B. A.; Dannenberg, J. J. J. Org. Chem. 1991, 56, 4853.
16. 2-Ar and gauche in Ar-S-S-Ar and Ar-BH-BH-Ar. The values were not corrected for zeropoint energy contributions.
17. Hansch, C.; Leo, A.; Taft, R. W. Chem. Rev. 1991, 91, 165.