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Issue 5, 2004
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The observation of a large gauche preference when 2-fluoroethylamine and 2-fluoroethanol become protonated

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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.

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

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Article information


Submitted
03 Oct 2003
Accepted
15 Dec 2003
First published
02 Feb 2004

Org. Biomol. Chem., 2004,2, 732-740
Article type
Paper

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

C. R. S. Briggs, M. J. Allen, D. O'Hagan, D. J. Tozer, A. M. Z. Slawin, A. E. Goeta and J. A. K. Howard, Org. Biomol. Chem., 2004, 2, 732 DOI: 10.1039/B312188G

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