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Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy
- Source :
- Chinese Journal of Magnetic Resonance, Vol 36, Iss 04, Pp 525-533 (2019)
- Publication Year :
- 2019
- Publisher :
- Science Press, 2019.
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Abstract
- A C2-symmetric host (host 1) was synthesized by derivatization of chiral diphenylethylenediamine with phenylisocyanate. High-resolution proton nuclear magnetic resonance (1H NMR) was used to investigate whether the chiral host could be used for enantiomeric discrimination of its structural analogues:α-phenylethylamine (guest 2), α-(p-methoxyphenyl)ethylamine (guest 9) and their derivatives (guests 3~8 and 10~13), and hydrogen-bonding interactions underlying the enantiomeric discrimination. It was observed that the host was able to recognize the urea and amide derivatives of the two primary amines, except for guests 7 and 12 bearing two NO2 groups. The host had stronger hydrogen-bonding interactions with the urea derivatives of guests 2 and 9 than with the corresponding amide derivatives, and high enantiomeric discrimination ability for the CHCH3 groups of the (R)- and (S)-urea derivatives.
Details
- Language :
- Chinese
- ISSN :
- 10004556
- Volume :
- 36
- Issue :
- 04
- Database :
- Directory of Open Access Journals
- Journal :
- Chinese Journal of Magnetic Resonance
- Publication Type :
- Academic Journal
- Accession number :
- edsdoj.36a9de4ce54a2f891b81ba370f871f
- Document Type :
- article
- Full Text :
- https://doi.org/10.11938/cjmr20182703