The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 2000, Pages 605-607

  O'Hagan, David ^a   Bilton, Clair ^a   Howard, Judith A K ^a   Knight, Lee ^a   Tozer, David J ^a  

^a DURHAM UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; CONFORMATIONS; MOLECULAR STRUCTURE; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL); X RAY ANALYSIS;

FLUORINE AMIDE; FLUOROETHYLAMIDES; GAUCHE EFFECT; X RAY STRUCTURE ANALYSIS;

FLUORINE COMPOUNDS;

EID: 0034175168     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b000205o     Document Type: Article

References (14)

1. D. O'Hagan and H. S. Rzepa, Chem. Commun., 1997, 645.
2. A. Bondi, J. Phys. Chem., 1964, 68, 441.
3. J. W. Banks, A. S. Batsanov, J. A. K. Howard, D. O'Hagan, H. S. Rzepa and S. Martin-Santamaria, J. Chem. Soc., Perkin Trans. 2, 1999, 2409.
4. S. K. Holmgren, K. M. Taylor, L. E. Bretcher and R. T. Raines, Nature, 1998, 392, 666.
5. S. K. Holmgren, L. E. Bretcher, K. M. Taylor and R. T. Raines, Chem. Biol., 1999, 6, 63.
6. N. C. Craig, A. Chen, K. H. Suh, S. Klee, G. C. Mellau, B. P. Winnewisser and M. Winnewisser, J. Am. Chem. Soc., 1997, 119, 4789.
7. R. D. Amos, N. C. Handy, P. G. Jones, A. J. Kirby, J. K. Parker, J. M. Percy and M. D. Su, J. Chem. Soc., Perkin Trans. 2, 1992, 549.
8. P. R. Rablen, R. W. Hoffmann, D. A. Hrovat and W. T. Borden, J. Chem. Soc., Perkin Trans. 2, 1999, 1719.
9. B. A. Phillips, G. Fodor, J. Gal, F. Letourneau and J. J. Ryan, Tetrahedron, 1973, 29, 3309.
10. W. Kohn and L. J. Sham, Phys. Rev., 1965, 140, A1133.
11. R. D. Amos, I. L. Alberts, J. S. Andrews, S. M. Colwell, N. C. Handy, D. Jayatilaka, P. J. Knowles, R. Kobayashi, G. J. Laming, A. M. Lee, P. E. Maslen, C, W. Murray, P. Palmieri, J. E. Rice, E. D. Simandiras, A. J. Stone, M.-D. Su and D. J. Tozer, 1995, CADPAC6.0, The Cambridge Analytic Derivatives Package (Cambridge, UK).
12. P. J. Stephens, F. J. Devlin, C. F. Chabalowski and M. J. Frisch, J. Phys. Chem., 1994, 98, 11623.
13. M. J. Frisch, J. A. Pople and J. S. Binkley, J. Chem. Phys., 1984, 80, 3265, and references cited therein.
14. J. R. Durig, J. Liu, T. S. Little and V. F. Kalasinsly, J. Phys. Chem., 1992, 96, 8224.