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Issue 4, 2000
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The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect

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Abstract

Experimental and theoretical data indicate a preferred conformation for N-β-fluoroethylamides in which the C–F and C–N(CO) bonds are gauche rather than anti to each other. Theoretical calculations on a model system predict the gauche conformation to be 1.8 kcal mol−1 lower in energy than the anti conformation. This compares with a value of 0.7 kcal mol−1 for the gauche effect in 1,2-difluoroethane.

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Supplementary files

Article information


Submitted
11 Jan 2000
Accepted
10 Feb 2000
First published
29 Jan 2000

J. Chem. Soc., Perkin Trans. 2, 2000, 605-607
Article type
Communication

The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect

D. O'Hagan, C. Bilton, J. A. K. Howard, L. Knight and D. J. Tozer, J. Chem. Soc., Perkin Trans. 2, 2000, 605 DOI: 10.1039/B000205O

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