Effect of Fluorine Substitution on the Carbon Acidity of Methane, Methyl Isocyanide, Acetonitrile, Acetaldehyde, and Nitromethane

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3937-3942

  Castejon, Henry J ^a   Wiberg, Kenneth B ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000590650     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9722818     Document Type: Article

References (16)

1. Wiberg, K. B.; Castejon, H. J. J. Org. Chem. 1995, 60, 6327.
2. Raabe, G.; Gais, H.-J.; Fleischauer, J. J. Am. Chem. Soc. 1996, 118, 4622. They examined the effect of fluorine substitution remote from the anionic center.
3. For a comparison with the other weak acids, dimethyl sulfone is more acidic than methane by 41 kcal/mol, and the rotational barrier is 9 kcal/mol (Wiberg, K. B.; Castejon, H. J. Am. Chem. Soc. 1994, 116, 10489).
4. Lias, S. G.; Bartmess, J. E.; Liebman, J. F.; Holmes, J. L.; Levin, R. D.; Mallard, W. G. J. Phys. Chem. Ref. Data 1988, 117, Suppl. 1.
5. Cioslowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1991, 113, 4142. Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
6. Cioslowski, J.; Mixon, S. T. J. Am. Chem. Soc. 1991, 113, 4142. Wiberg, K. B.; Hadad, C. M.; Rablen, P. R.; Cioslowski, J. J. Am. Chem. Soc. 1992, 114, 8644.
7. Wiberg, K. B.; Schleyer, P. v. R.; Streitwieser, A. Can. J. Chem. 1996, 74, 892.
8. Ellison, G. B.; Engleking, P. C.; Lineberger, W. C. J. Am. Chem. Soc. 1978, 100, 2556.
9. Bent, H. Chem. Rev. 1961, 61, 275.
10. Dill, J. D.; Schleyer, P. v. R.; Pople, J. A. J. Am. Chem. Soc. 1976, 98, 1663.
11. Wiberg, K. B.; Rablen, P. R. J. Am. Chem. Soc. 1993, 115, 614.
12. Cioslowski, J.; Nanayakkara, A. J. Am. Chem. Soc. 1993, 115, 11213. Guadagnini, P. H.; Bruns, R. E. J. Am. Chem. Soc. 1995, 117, 4144.
13. Cioslowski, J.; Nanayakkara, A. J. Am. Chem. Soc. 1993, 115, 11213. Guadagnini, P. H.; Bruns, R. E. J. Am. Chem. Soc. 1995, 117, 4144.
14. Politzer, P.; Heheey, J. E.; Murray, J. S.; Grodzicki, M. J. Mol. Struct. 1992, 259, 99.
15. Frisch, M. J.; Trucks; G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb; M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. A.; Montgomery, J. A.; Raghavachari, K.; Al-Laham, M. A.; Zakrzewski, V. G.; Ortis, J. V.; Foresman, J. B.; Cioslowski, J.; Sefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y.; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 95, Development Version (Rev. D), Gaussian, Inc., Pittsburgh, PA, 1995.
16. Keith, T. A. Yale University. This is based on PROAIM: Biegler- König, F. W.; Bader, R. F. W.; Tang, T.-H. J. Comput. Chem. 1982, 3, 317.