Author(s)

C. R. S. Briggs, M. J. Allen, D. O'Hagan, D. J. Tozer, A. M. Z. Slawin, A. E. Goeta, J. A. K. Howard

ISBN

1477-0520

Publication year

2004

Periodical

Organic & Biomolecular Chemistry

Periodical Number

5

Volume

2

Pages

732-740

Author Address

Full version

The energies of the gauche and anti conformers of 2-fluoroethylamine, 2-fluoroethanol and their protonated analogues are calculated using density functional theory. Unlike the non protonated systems, the protonated systems show a strong gauche effect where the C-F and the C-+NH3 or C-F and C-+OH2 bonds are gauche rather than anti to each other. Single crystal X-ray diffraction studies of 2-fluoroethylammonium compounds identify the same conformational preference.