THE STRUCTURE OF ADDUCTS OF THE THREE DIASTEREOISOMERIC 1,4:3,6-DIANHYDROHEXITOLS AND LANTHANIDE CHELATES IN ACETONE

Article abstract of DOI:10.1016/S0040-4020(01)91298-0

Gd(dpm)₃ induced 1H and 13C relaxation rate enhancements showed that 1,4:3,6-dianhydro-D-glucitol (containing both a threo and an erythro -O-C-C-OH moiety) acts as a bidentate ligand for Gd(dpm)₃.Coordination occurs selectively with the erythro -O-C-C-OH moiety, involving the endohydroxyl group at C⁵ and the neighbouring ether oxygen.From a comparison of the Eu(fod)₃ induced 1H shifts of 1,4:3.6-dianhydro-D-glucitol with those of 1,4:3,6-dianhydro-D-mannitol and 1,4:3,6-dianhydro-L-iditol it is concluded that the mannitol derivative (containing two erythro -O-C-C-OH moieties) forms analogous adducts, whereas the iditol derivative (containing two threo -O-C-C-OH moeities) has a low association constant.