The interaction of some carbohydrate derivatives with sodium ions in acetone solution

Abstract

The changes induced in the chemical shifts of certain protons in some carbohydrate derivatives and some other poly-oxygenated compounds, on addition of sodium iodide to their solutions in acetone- d 6, are reported. The H-1 resonances of β-glycosides of 2,3- O-isopropylidene-4- O-methyl- L-rhamnopyranoside were significantly affected by the addition of sodium ions, whereas with the α- L-glycosides, these resonances were virtually unaltered. Methoxyacetaldehyde diethyl acetal, triethyl orthoformate, and tris(2-methoxyethyl) orthoformate all showed significant induced-shifts in their acetal-proton resonances on the addition of sodium ions, and all the proton resonances of 1,4-anhydroerythritol were affected, but to differing degrees. With the cis- and trans-5-methoxy-2-phenyl-1,3-dioxanes, it is the former isomer, which can in principle simultaneously use all three oxygen atoms in the molecule to complex a sodium ion, which shows the greatest induced-shift in the acetal-proton resonance.