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)

Abstract

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.
• Status: Published
• Refereed: Yes
• 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: 0040-4039
• ISSN (Online): 1873-3581