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Unambiguous full multinuclear NMR assignment of 4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracycylophane & NMR differentiation of its enantiomers, and related compounds

by Sheryl Rabinowitz

Institution: Rutgers University
Department: Chemistry
Degree: MS
Year: 2013
Keywords: Nuclear magnetic resonance; Chirality; Cyclophanes
Posted:
Record ID: 1999611
Full text PDF: http://hdl.rutgers.edu/1782.1/rucore10005600001.ETD.000067579


Abstract

For the first time the full multinuclear ¹H, ¹³C, and ¹⁹F assignments were established for 4-amino-1,1,2,2,9,9,10,10-octafluoro[2.2]paracyclophane (OFP-NH2). These were achieved by using a combination of 1D, COSY, and HETCOR NMR techniques. The assignments were later confirmed by nOe experiments. The interaction of OFP-NH₂ with different chiral shift reagents was explored, and it was shown that it is possible to clearly detect both enantiomers of the planar chiral OFP-NH₂ (in both the ¹H and ¹⁹F NMR). This method of chiral discrimination was also shown to be applicable to other similar chiral OFP derivatives.

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