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首页> 外文期刊>Chemistry: A European journal >Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction
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Liquid-Crystalline Ionic Liquids as Ordered Reaction Media for the Diels-Alder Reaction

机译：液晶离子液体作为Diels-Alder反应的有序反应介质

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Liquid-crystalline ionic liquids (LCILs) are ordered materials that have untapped potential to be used as reaction media for synthetic chemistry. This paper investigates the potential for the ordered structures of LCILs to influence the stereochemical outcome of the Diels-Alder reaction between cyclopentadiene and methyl acrylate. The ratio of endo-to exo-product from this reaction was monitored for a range of ionic liquids (ILs) and LCILs. Comparison of the endo: exo ratios in these reactions as a function of cation, anion and liquid crystallinity of the reaction media, allowed for the effects of liquid crystallinity to be distinguished from anion effects or cation alkyl chain length effects. These data strongly suggest that the proportion of exo-product increases as the reaction media is changed from an isotropic IL to a LCIL. A detailed molecular dynamics (MD) study suggests that this effect is related to different hydrogen bonding interactions between the reaction media and the exo-and endo-transition states in solvents with layered, smectic ordering compared to those that are isotropic.
机译：液晶离子液体（LCIL）是有序材料，具有未被开发的潜力，可用作合成化学的反应介质。本文研究了LCIL的有序结构可能影响环戊二烯与丙烯酸甲酯之间Diels-Alder反应的立体化学结果的可能性。监测该反应的内产物与外产物的比例，以检测一系列离子液体（IL）和LCIL。在这些反应中内，外比的变化作为反应介质的阳离子，阴离子和液晶性的函数，可以将液晶性的影响与阴离子作用或阳离子烷基链长效应区分开。这些数据强烈表明，随着反应介质从各向同性IL变为LCIL，外生产物的比例增加。一项详细的分子动力学（MD）研究表明，与各向同性的溶剂相比，这种影响与反应介质与层状，近晶顺序的溶剂中的外向和内向过渡态之间不同的氢键相互作用有关。

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