Fluoride-Induced Elimination of Ethyl Fluoride. The Importance of High-Level Optimizations in ab Iniiio and DFT Studies

Journal of Organic Chemistry

Volumn 60, Issue 3, 1995, Pages 488-489

  Gronert, Scott ^a   Merrill, Grant N ^b   Kass, Steven R ^b,c  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c ALFRED P SLOAN FOUNDATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001206228     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00108a005     Document Type: Article

References (19)

1. Gronert, S. J. Am. Chem. Soc. 1993, 115, 652.
2. Gronert, S. J. Am. Chem. Soc. 1992, 114, 2349.
3. Gronert, S. J. Am. Chem. Soc. 1991, 113, 6041.
4. Minato, T.; Yamabe, S. J. Am. Chem. Soc. 1988, 110, 4586.
5. Minato, T.; Yamabe, S. J. Am. Chem. Soc. 1985, 107, 4621.
6. Pross, A.; Shaik, S. S. J. Am. Chem. Soc. 1982, 104, 187.
7. Bach, R. D.; Badger, R. C.; Lang, T. J. J. Am. Chem. Soc. 1979, 101, 2845.
8. Bickelhaupt, F. M.; Baerends, E. J.; Nibbering, N. M. M.; Ziegler, T. J. Am. Chem. Soc. 1993, 115, 9160.
9. For F_ + ethyl fluoride, the reaction to give CH2=CH2, HF, and F_ is endothermic by 10.4 kcal/mol. For experimental data, see: Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D. J. Phys. Chem. Ref. Data 1988, 17, Suppl. 1. The slightly updated form is available on a personal computer, NIST Negative Ion Energetics Database (Version 3.00, 1993), NIST Standard Reference Database 19B.
10. Gronert, S. J. Am. Chem. Soc. 1993, 115, 10258.
11. All of the reported calculations, unless otherwise noted, weee carried out using Gaussian 92, Revision G.2: 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.
12. Slater, J. C. The Self-Consistent Field for Molecules and Solids 0Quantum Theory of Molecules and Solids); McGraw-Hill: New York, 1974; Vol. 4.
13. For example, see: Larson, J. W.; McMahon, T. B. Inorg. Chem. 1984, 23, 2029.
14. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Binkley, J. S.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654.
15. Hariharan, P. C.; Pople, J. A. Theor. Chim. Acta 1973, 28, 213.
16. Becke, A. D. Phys. Rev. A 1988, 38, 3098.
17. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
18. For details about the aug-cc-pVDZ basis set see: Kendall, R. A.; Dunning, T. H., Jr.; Harrison, R. S. J. Chem. Phys. 1992, 96, 6796.
19. Ridge, D. P.; Beauchamp, J. L. J. Am. Chem. Soc. 1974, 96, 3595.