Application of aromatic amide-derived atropisomers as chiral solvating agents for discrimination of optically active mandelic acid derivatives in 1H nuclear magnetic resonance spectroscopy,Magnetic Resonance in Chemistry

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Application of aromatic amide-derived atropisomers as chiral solvating agents for discrimination of optically active mandelic acid derivatives in 1H nuclear magnetic resonance spectroscopy
Magnetic Resonance in Chemistry ( IF 1.9 ) Pub Date : 2021-06-09 , DOI: 10.1002/mrc.5185
Xiaojing Zheng ₁ , Tingfeng Tang ₁ , Li Li ₂ , Li-Wen Xu ₂ , Shaohua Huang _{1,

3} , Yufen Zhao _{1,

3}

Affiliation

Non-biaryl atropisomers and their stereochemistry have attracted much attentions in the past years. However, application of the non-biaryl atropisomers as chiral solvating agents is yet to be explored. In this work, four aromatic amide-derived atropisomeric phosphine ligands (hosts) were used as chiral solvating agents to recognize various mandelic acid derivatives (guests) in ¹H nuclear magnetic resonance (NMR) spectroscopy. It is found that chiral center configurations of the four hosts have different effects on the enantiorecognition to the used guests. In addition, the host and guest interaction was further investigated by determination of the host–guest complex stoichiometry using the Job's method and density functional theory calculation, respectively. Moreover, chiral analysis accuracy of these hosts was evaluated through relationship between enantiomeric excess values of 4-chloromandelic acid provided by NMR and gravimetry, respectively.

中文翻译：

芳香酰胺衍生的阻转异构体作为手性溶剂化剂在 1H 核磁共振光谱中区分旋光扁桃酸衍生物的应用

非联芳基阻转异构体及其立体化学在过去几年引起了广泛关注。然而，非联芳基阻转异构体作为手性溶剂化剂的应用还有待探索。在这项工作中，四芳族酰胺衍生的阻转异构体的膦配体（主机）被用作手性溶解剂中，以识别各种扁桃酸衍生物（客人）¹H 核磁共振 (NMR) 光谱。发现四个宿主的手性中心配置对使用的客人的对映识别有不同的影响。此外，通过分别使用 Job 方法和密度泛函理论计算确定主客体复杂的化学计量，进一步研究了主体和客体的相互作用。此外，这些主体的手性分析准确性分别通过 NMR 和重量分析提供的 4-氯扁桃酸对映体过量值之间的关系进行评估。

更新日期：2021-06-09

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