The preferred conformation of N-β-fluoroethylamides. Observation of the fluorine amide gauche effect
- 29 January 2000
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 4,p. 605-607
- https://doi.org/10.1039/b000205o
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.Keywords
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