Lanthanide-Cyclodextrin Complexes as Probes for Elucidating Optical Purity by NMR Spectroscopy
نویسندگان
چکیده
A multidentate ligand is bonded to cyclodextrins by the reaction of diethylenetriaminepentaacetic dianhydride with 6-monoand 2-mono(ethylenediamine) derivatives of cyclodextrin. Adding Dy(II1) to the cyclodextrin derivatives enhances the enantiomeric resolution in the IH N M R spectra of carbinoxamine maleate, doxylamine succinate, pheniramine maleate, propranolol hydrochloride, and tryptophan. The enhancement is more pronounced with the secondary derivative. The Dy(II1)-induced shifts can be used to elucidate the geometry of cyclodextrin-substrate inclusion complexes. Lanthanide-induced shifts are reported for complexes of aspartame, tryptophan, propranolol, and 1 -anilino-8-naphthalenesulfonate with cyclodextrins, and the relative magnitudes of the shifts agree with previously reported structures of the complexes.
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