Cyclodextrins as chiral nuclear magnetic resonance shift reagents

MacNicol, D. D. and Rycroft, D. S. (1977) Cyclodextrins as chiral nuclear magnetic resonance shift reagents. Tetrahedron Letters, 18(25), pp. 2173-2176. (doi: 10.1016/S0040-4039(01)83711-4)

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Although chemical shift non-equivalence between enantiotopic groups in n.m.r. spectra has often been observed employing optically active solvents or chiral lanthanide shift reagents, or when a substrate is complexed to a chiral crown compound, such methods are normally critically dependent upon suitable substrate functionality. We now report that guest binding within the chiral cavity of β-cyclodextrin in D2O provides a method for inducing 19F n.m.r. chemical shifts between the prochiral CF3 groups of compounds 1 [1,1,1,3,3,3-hexafluoro-2-phenyl-2-propanol] and 2 [1,1,1,3,3,3-hexafluoro-2-(p-tolyl)propane], it being particularly noteworthy that the latter molecule lacks the type of functional group usually required for such chiral effects.

Item Type:Articles
Keywords:NMR spectroscopy.
Glasgow Author(s) Enlighten ID:Rycroft, Dr David and MacNicol, Dr David
Authors: MacNicol, D. D., and Rycroft, D. S.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
Publisher:Pergamon Press Ltd
ISSN (Online):1873-3581

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