Effect of fluorine substitution on the energies of small ring compounds

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2932-2938

  Wiberg, Kenneth B ^a   Marquez, Manuel ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE; FLUORINE; PROPYLENE;

ARTICLE; CHEMICAL BINDING; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0032054963     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja971413b     Document Type: Article

References (45)

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23. 2 = 1.332(6), C-C = 1.441(6) , C=C = 1.312 (Norden, T. D.; Staley, S. W.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1986, 108, 7912). Cyclopropanone: C1-C3 = 1.475(17), C2-C3 = 1.575(12), C=O = 1.191(21) (Pochen, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896). 1,1-Difluorocyclopropane: C1-C2 = 1.464(2), C2-C3 = 1.553(1), C-F = 1.358(2) (Perretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2469). 1,1-Difluorocyclopropene: C-C = 1.438 (7), C=C = 1.321(1), C-F = 1.365(5) ((Ramaprasad, K. R.; Laurie, V. W.; Craig, N. C. J. Chem. Phys. 1976, 64, 4832).
24. 2 = 1.332(6), C-C = 1.441(6) , C=C = 1.312 (Norden, T. D.; Staley, S. W.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1986, 108, 7912). Cyclopropanone: C1-C3 = 1.475(17), C2-C3 = 1.575(12), C=O = 1.191(21) (Pochen, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896). 1,1-Difluorocyclopropane: C1-C2 = 1.464(2), C2-C3 = 1.553(1), C-F = 1.358(2) (Perretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2469). 1,1-Difluorocyclopropene: C-C = 1.438 (7), C=C = 1.321(1), C-F = 1.365(5) ((Ramaprasad, K. R.; Laurie, V. W.; Craig, N. C. J. Chem. Phys. 1976, 64, 4832).
25. 2 = 1.332(6), C-C = 1.441(6) , C=C = 1.312 (Norden, T. D.; Staley, S. W.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1986, 108, 7912). Cyclopropanone: C1-C3 = 1.475(17), C2-C3 = 1.575(12), C=O = 1.191(21) (Pochen, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896). 1,1-Difluorocyclopropane: C1-C2 = 1.464(2), C2-C3 = 1.553(1), C-F = 1.358(2) (Perretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2469). 1,1-Difluorocyclopropene: C-C = 1.438 (7), C=C = 1.321(1), C-F = 1.365(5) ((Ramaprasad, K. R.; Laurie, V. W.; Craig, N. C. J. Chem. Phys. 1976, 64, 4832).
26. 2 = 1.332(6), C-C = 1.441(6) , C=C = 1.312 (Norden, T. D.; Staley, S. W.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1986, 108, 7912). Cyclopropanone: C1-C3 = 1.475(17), C2-C3 = 1.575(12), C=O = 1.191(21) (Pochen, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896). 1,1-Difluorocyclopropane: C1-C2 = 1.464(2), C2-C3 = 1.553(1), C-F = 1.358(2) (Perretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2469). 1,1-Difluorocyclopropene: C-C = 1.438 (7), C=C = 1.321(1), C-F = 1.365(5) ((Ramaprasad, K. R.; Laurie, V. W.; Craig, N. C. J. Chem. Phys. 1976, 64, 4832).
27. 2 = 1.332(6), C-C = 1.441(6) , C=C = 1.312 (Norden, T. D.; Staley, S. W.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1986, 108, 7912). Cyclopropanone: C1-C3 = 1.475(17), C2-C3 = 1.575(12), C=O = 1.191(21) (Pochen, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896). 1,1-Difluorocyclopropane: C1-C2 = 1.464(2), C2-C3 = 1.553(1), C-F = 1.358(2) (Perretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2469). 1,1-Difluorocyclopropene: C-C = 1.438 (7), C=C = 1.321(1), C-F = 1.365(5) ((Ramaprasad, K. R.; Laurie, V. W.; Craig, N. C. J. Chem. Phys. 1976, 64, 4832).
28. 2 = 1.332(6), C-C = 1.441(6) , C=C = 1.312 (Norden, T. D.; Staley, S. W.; Taylor, W. H.; Harmony, M. D. J. Am. Chem. Soc. 1986, 108, 7912). Cyclopropanone: C1-C3 = 1.475(17), C2-C3 = 1.575(12), C=O = 1.191(21) (Pochen, J. M.; Baldwin, J. E.; Flygare, W. H. J. Am. Chem. Soc. 1969, 91, 1896). 1,1-Difluorocyclopropane: C1-C2 = 1.464(2), C2-C3 = 1.553(1), C-F = 1.358(2) (Perretta, A. T.; Laurie, V. W. J. Chem. Phys. 1975, 62, 2469). 1,1-Difluorocyclopropene: C-C = 1.438 (7), C=C = 1.321(1), C-F = 1.365(5) ((Ramaprasad, K. R.; Laurie, V. W.; Craig, N. C. J. Chem. Phys. 1976, 64, 4832).
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38. The total energies and zero-point energies are available as Supporting Information.
39. Wiberg, K. B.; Rablen, P. R. To be published.
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