| 核磁共振氢谱中二苯基乙二胺衍生物手性识别其结构类似物 |
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| 引用本文： | 杨盈,黄少华,冯继文.核磁共振氢谱中二苯基乙二胺衍生物手性识别其结构类似物[J].波谱学杂志,2019,36(4):525-533. |
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| 作者姓名： | 杨盈 黄少华 冯继文 |
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| 作者单位： | 1. 宁波大学 新药技术研究院, 浙江 宁波 315211;2. 中国科学院 青岛生物能源与过程研究所, 山东 青岛 266101;3. 波谱与原子分子物理国家重点实验室, 中国科学院 武汉物理与数学研究所, 湖北 武汉 430071 |
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| 基金项目： | the National Natural Science Foundation of China (21105108); the Key Technology Talent Program of Chinese Academy of Sciences (2015). |
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| 摘 要： | 本文通过手性二苯基乙二胺与异氰酸酯的衍生化反应，合成了一种C2对称的手性主体1.该主体可以手性识别其结构类似物：α-苯乙胺（客体2）、α-对甲氧基苯乙胺（客体9）以及它们的衍生物（客体3~8和10~13）.高分辨核磁共振氢谱（1H NMR）显示了对映体识别中主客体间的氢键作用.结果表明，除含2个NO2的客体7和12外，主体1可以较易识别含有两个伯胺的脲和酰胺衍生物.研究还发现，主体1对脲衍生物2、9比对酰胺衍生物有更强的氢键作用，此外主体1对（R）和（S）-脲衍生物中的CHCH3基团也有更高的辨识能力.
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| 关 键 词： | 二苯基乙二胺 衍生物 对映体识别 核磁共振(NMR)波谱 |
| 收稿时间： | 2018-12-19 |
Mechanisms Underlying Enantiomeric Discrimination of Its Structural Analogues with a Diphenylethylenediamine Derivative Revealed by Proton NMR Spectroscopy |
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| 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. |
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| Authors: | YANG Ying HUANG Shao-hua FENG Ji-wen |
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| Institution: | 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 |
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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. |
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| Keywords: | diphenylethylenediamine derivative enantiomeric discrimination nuclear magnetic resonance (NMR) spectroscopy |
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