Configurational and conformational insights on exo- and en do-1, 4:3, 6-dianhydroglucitol mononitrate

A PMR study of the 1,4:3,6-dianhydroglucitol mononitrates allows the easy attribution of the 2-exo- or 5-endo nitrate configuration to each of the isomers. Coupling data obtained in chloroform and in pyridine provide insight into their conformations. The solvent shifts indicate a hydrogen bridged solute-solvent complex in the exo-compound, but a random solvation for the endo-nitrate.