Journal of the American Chemical Society, Vol.123, No.50, 12605-12610, 2001
Solvent effect on the isomeric equilibrium of carbohydrates: The superior ability of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization
The higher aptitude of 2,2,2-trifluoroethanol for intramolecular hydrogen bond stabilization in carbohydrates is suggested. This belief, arising from the analysis by H-1 NMR spectroscopy of the solvent effect of D2O, DMSO-d(6), and 2,2,2-trifluoroethanol-d(3) on the isomeric equilibrium of caryophyllose, was also confirmed by shifting of the conformational equilibria of beta -ribopyranose and of its methyl glycoside.