Alex J. Roche, Sheryl A. Rabinowitz, Kasey Cox
Nov 30, 2013
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Influential Citations
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Journal
Tetrahedron-asymmetry
Abstract
Abstract A selection of amino-substituted 1,1,2,2,9,9,10,10 octafluoro[2.2]paracyclophanes were tested for enantiodiscrimination by 1 H and 19 F NMR spectroscopy via their interaction with different lanthanide tris β-diketonate chiral shift reagents. The amino-, and the pseudo- ortho di-amino substituted octafluoro[2.2]paracyclophanes, both of which exhibit planar chirality, revealed significant shifts and splittings of various 1 H and 19 F NMR signals upon the addition of the chiral shift reagents, which allowed the easy determination of the enantiomeric purity. When the chiral shift reagent was added to an inseparable mixture of the (chiral) pseudo- meta , and (achiral) pseudo- para diamino analogues, both the chiral and achiral molecules revealed NMR doubling. In the case of the achiral molecule, this NMR behavior is due to the meso nature of the pseudo- para species.