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 1H NMR spectroscopy of the solvent effect of D2O, DMSO-d6, and 2,2,2-trifluoroethanol-d3 on the isomeric equilibrium of caryophyllose, was also confirmed by shifting of the conformational equilibria of beta-ribopyranose and of its methyl glycoside.
Molinaro
A
A
Department of Organic Chemistry and Biochemistry, University Federico II, Complesso Universitario Monte S'Angelo, Via Cintia 4, 80126 Napoli, Italy. molinaro@unina.it
De Castro
C
C
Lanzetta
R
R
Manzo
E
E
Parrilli
M
M
D002236:Carbohydrate Conformation; D017666:Deuterium Oxide / Q000737:chemistry; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D006860:Hydrogen Bonding; D007700:Kinetics; D009005:Monosaccharides / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011134:Polysaccharides / Q000737:chemistry; D012266:Ribose / Q000737:chemistry*; D012997:Solvents; D014270:Trifluoroethanol / Q000737:chemistry*
D009005:Monosaccharides; D011134:Polysaccharides; D012997:Solvents; C441250:caryophyllan; C439355:methyl -caryophylloside; D012266:Ribose; D014270:Trifluoroethanol; D017666:Deuterium Oxide; D004121:Dimethyl Sulfoxide