B. Adams et Le. Lerner, EFFECT OF STEREOCHEMISTRY ON HYDROXYL PROTON CHEMICAL-SHIFTS AND COUPLING-CONSTANTS IN CARBOHYDRATES, Magnetic resonance in chemistry, 32(4), 1994, pp. 225-230
Chemical shifts and coupling constants of hydroxyl protons for a serie
s of simple carbohydrates are reported and several trends extracted: (
1) chemical shifts are relatively independent of the experimental cond
itions if referenced to water; (2) chemical shifts are sensitive to th
e orientation of the HO group and its neighbors; and (3) coupling cons
tants fall within a relatively narrow range, which is indicative of ro
tational averaging. These observations suggest that NMR parameters of
hydroxyl protons can provide important diagnostic information about th
e stereochemistry of simple carbohydrates and may prove useful for ana
lysis of more complex compounds.