The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated
- 2 February 2004
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 2 (5) , 732-740
- https://doi.org/10.1039/b312188g
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.Keywords
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