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The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated

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

Abstract:
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.

Full version: Available here

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ISBN: 1477-0520
Publication Year: 2004
Periodical: Organic & Biomolecular Chemistry
Periodical Number: 5
Volume: 2
Pages: 732-740
Author Address: