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Cyclodextrins as chiral complexing agents in water, and their application to optical purity measurements
Author(s) -
Greatbanks David,
Pickford Roderick
Publication year - 1987
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1260250306
Subject(s) - chemistry , diastereomer , cyclodextrin , observable , chemical shift , inclusion compound , hydrochloride , stereochemistry , computational chemistry , organic chemistry , physics , quantum mechanics
The interaction of β‐cyclodextrin with propanolol hydrochloride was shown by NMR to produce diastereomeric pairs observable in D 2 O solution at 400 MHz. By addition of racemate to pure (–)‐isomer, the usefulness of this novel technique in being able to measure optical purity in water down to the 1% level was demonstrated. Using changes in chemical shifts and NOE effects, a possible structure for the inclusion complex is proposed. γ‐Cyclodextrin induced larger shifts in the spectrum than the β‐equivalent, whereas α‐cyclodextrin had no effect.