High-resolution solid-state NMR spectroscopy as a tool for investigation of enantioselective inclusion complexation.
In this paper, we showed the application of solid state-NMR (SS NMR) spectroscopy in structural studies of chiral compounds employing sample of (E)-1-diphenylphosphinoylpent-3-en-2-ol 1 as a model compound. Racemate of 1 was fully characterized by NMR techniques (both in liquid and solid phase) and X-ray crystallography. Theoretical calculations employing the GIAO approach were used to explain the influence of hydrogen bonding on 31P NMR shielding parameter in racemate. Enantioselective inclusion complexation (EIC) method with TADDOL as host molecule was applied to separate of enantiomers. The formation of host-guest complex and decomplexation procedure was monitored by means of the SS NMR. The liquid-state NMR, due to similarity of 13C and 31P spectral parameters was not able to distinguish racemate from enantiomer. In the solid phase, owing to distinction of hydrogen bonding and molecular packing in the crystal lattice, racemate and enantiomers were easy recognized by NMR spectroscopy.
Gajda
J
J
Polish Academy of Sciences, Center of Molecular and Macromolecular Studies, Sienkiewicza 112, 90-363 Łódź, Poland.
Jeziorna
A
A
Ciesielski
W
W
Potrzebowski
W M
WM
Prezdo
W W
WW
Potrzebowski
M J
MJ