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Chiral discrimination of amines by anisotropic NMR parameters using chiral polyacrylamide-based gels.

MPS-Authors
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Schmidt,  M.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Sun,  H.
Department of NMR based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Leonov,  A.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Griesinger,  C.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Reinscheid,  U. M.
Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society;

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Supplementary Material (public)

1795852_Supplement_1.doc
(Supplementary material), 3MB

Citation

Schmidt, M., Sun, H., Leonov, A., Griesinger, C., & Reinscheid, U. M. (2012). Chiral discrimination of amines by anisotropic NMR parameters using chiral polyacrylamide-based gels. Magnetic Resonance in Chemistry, 50(Supplement 1), S38-S44. doi:10.1002/mrc.3886.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0013-F0CB-2
Abstract
A new chiral alignment medium for dimethyl sulfoxide, methanol, and water as solvents was developed. Because both enantiomers of the gel are available, it is possible to enantiodiscriminate natural products such as strychnine HCl that naturally occurs as single enantiomer. With the two methods of achieving anisotropy, namely stretching and confinement, the degree of alignment can be adjusted, and the director changed from horizontal to vertical. This increases the applicability. Three compounds were enantiodiscriminated on the basis of residual dipolar coupling data: mefloquine HCl, strychnine HCl, and menthylamine HCl.