Articles

Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy

  • YANG Ying ,
  • HUANG Shao-hua ,
  • FENG Ji-wen
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  • 1. Institute of Drug Discovery and Technology, Ningbo University, Ningbo 315211, China;
    2. Qingdao Institute of Bioenergy and Bioprocess Technology, Chinese Academy of Sciences, Qingdao 266101, China;
    3. State Key Laboratory of Magnetic Resonance and Atomic and Molecular Physics, Wuhan Institute of Physics and Mathematics, Chinese Academy of Sciences, Wuhan 430071, China

Received date: 2018-12-19

  Online published: 2019-02-26

Supported by

the National Natural Science Foundation of China (21105108); the Key Technology Talent Program of Chinese Academy of Sciences (2015).

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.

Cite this article

YANG Ying , HUANG Shao-hua , FENG Ji-wen . Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy[J]. Chinese Journal of Magnetic Resonance, 2019 , 36(4) : 525 -533 . DOI: 10.11938/cjmr20182703

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