The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated.
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-(+)NH(3) or C-F and C-(+)OH(2) bonds are gauche rather than anti to each other. Single crystal X-ray diffraction studies of 2-fluoroethylammonium compounds identify the same conformational preference.
School of Chemistry and Centre for Biomolecular Sciences, University of St. Andrews, North Haugh, St Andrews, UK KY16 9ST.
Caroline R S
CR
Briggs
Mark J
MJ
Allen
David
D
O'Hagan
David J
DJ
Tozer
Alexandra M Z
AM
Slawin
Andrés E
AE
Goeta
Judith A K
JA
Howard