Non-equivalence of vicinal proton–fluorine coupling constants in a CF3—CH2group

Autor: Fraser, Robert R., Hanbury, Paul
Zdroj: Canadian Journal of Chemistry; July 1967, Vol. 45 Issue: 13 p1485-1489, 5p
Abstrakt: The proton magnetic resonance spectrum of the tetrahydropyranyl ether of 2,2,2-trifluoroethanol has been measured in several solvents and at different temperatures. Analysis of the ABX3pattern produced by the trifluoroethyl group revealed a unique feature. Under all conditions, it was found that the vicinal coupling constants JAXand JBXhad different magnitudes. This non-equivalence is interpreted as evidence that the C—HAand C—HBbonds of the trifluoroethyl group differ electronically. A possible relation between this finding and the anomeric effect is discussed. In contrast to the above results, the tetrahydropyranyl ether of ethanol showed equal vicinal proton–proton coupling constants in the ethyl group.
Databáze: Supplemental Index