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首页> 外文期刊>Crystal growth & design >Solvent-Induced Chirality Switching in the Enantioseparation of Halogen-Substituted Mandelic Acids: Structural Effects on Molecular Packing
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Solvent-Induced Chirality Switching in the Enantioseparation of Halogen-Substituted Mandelic Acids: Structural Effects on Molecular Packing

机译：溶剂诱导的卤素取代伪胶酸映的肾上腺性切换：分子包装的结构效应

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摘要

The solvent effect on the enantioseparation of halogen-substituted mandelic acid derivatives via diastereomerit salt formation has been investigated. The diastereomeric salts of para-halogen-substituted mandelic acid derivatives (p-X-MA) were obtained with high efficiency. In addition, both diastereomeric salts of p-F-MA were successfully obtained by controlling the concentration of the acetone solution. Efficient solvent-induced chirality switching was generally observed for meta-halogen-substituted mandelic acid derivatives (m-X-MA). Water, aprotic solvents, and short-chain alcohols such as i-PrOH gave the (S)-salt, whereas the (R)-salt is preferentially formed from long-chain alcohols such as n-BuOH and s-BuOH. Crystallographic analysis of the salts showed that the inclusion of the alcohol solvent in the diastereomeric salts changed the hydrogen-bonding network and molecular packing. The molecular packing was dependent on the size of the halogen substituents and the solvent used. Finally, this technique has been successfully applied to the preparation of both pure enantiomers of m-Cl-MA.
机译：研究了对卤素取代的少杀盐衍生物通过非对映异构体盐形成的溶剂作用。得到对卤素取代的颗粒酸衍生物（P-X-MA）的非对映异构盐以高效率获得。此外，通过控制丙酮溶液的浓度成功地获得了P-F-MA的非对映异构体盐。通常观察到高效溶剂诱导的手性切换，用于使卤素取代的颗粒酸衍生物（M-X-MA）。水，非质子溶剂和短链醇等I-ProH给出了（S）-SALT，而（R）-SALT优先由长链醇如N-BuOH和S-BuOH形成。盐的晶体分析表明，在非对映异构盐中包含醇溶剂改变了氢键网络和分子包装。分子包装取决于卤素取代基的尺寸和所用的溶剂。最后，该技术已成功地应用于制备M-Cl-MA的纯对映体。

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  • 来源
    《Crystal growth & design》 |2019年第12期|共7页
  • 作者

    Kodama Koichi; Kawasaki Kozue; Yi Meng; Tsukarnoto Kaguya; Shitara Hiroaki; Hirose Takuji;

  • 作者单位

    Saitama Univ Grad Sch Sci &

    Engn Sakura Ku 255 Shimo Okubo Saitama 3388570 Japan;

    Saitama Univ Grad Sch Sci &

    Engn Sakura Ku 255 Shimo Okubo Saitama 3388570 Japan;

    Saitama Univ Grad Sch Sci &

    Engn Sakura Ku 255 Shimo Okubo Saitama 3388570 Japan;

    Saitama Univ Grad Sch Sci &

    Engn Sakura Ku 255 Shimo Okubo Saitama 3388570 Japan;

    Saitama Univ Tech Support Ctr Sakura Ku 255 Shimo Okubo Saitama 3388570 Japan;

    Saitama Univ Grad Sch Sci &

    Engn Sakura Ku 255 Shimo Okubo Saitama 3388570 Japan;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 晶体学;
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