1-methyl-3-octadecylimidazolium bis(trifluoromethylsulfonyl)amide | 404001-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-3-octadecylimidazolium bis(trifluoromethylsulfonyl)amide
• 英文别名: 1-octadecyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide；1-octadecyl-3-methylimidazolium bis(triflic)imide；[C18mim][Tf2N]；NSC747271；1-Methyl-3-octadecylimidazolium bis(trifluoromethylsulfonyl)imide；bis(trifluoromethylsulfonyl)azanide;1-methyl-3-octadecylimidazol-1-ium
• CAS: 404001-51-0
• 化学式: C₂F₆NO₄S₂*C₂₂H₄₃N₂
• 分子量: 615.746
• InChiKey: DMEDSJKEUMLSKF-UHFFFAOYSA-N

物化性质

• 熔点：
  54.0 °C
• 密度：
  1.15 g/cm3 (liquid)

计算性质

• 辛醇/水分配系数(LogP)：
  7.63
• 重原子数：
  39
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  94.8
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  硬脂基溴 以 氘代丙酮 、 丙酮 为溶剂， 反应 72.0h， 生成 1-methyl-3-octadecylimidazolium bis(trifluoromethylsulfonyl)amide
  参考文献：
  名称：

  Ionic liquid crystals based on 1-alkyl-3-methylimidazolium cations and perfluorinated sulfonylimide anions

  摘要：

  In contrast to the studies on ionic liquids based on perfluorinated sulfonylimide anions, their ionic liquid crystals were seldom reported. In the present study, four 1-alkyl-3-methylimidazolium perfluorinated sulfonylimide salts ([C(x)MIm][N(SO2RF)(2)], x = 18 and 22; R-F = F (FSI) and CF3(TFSI)) have been synthesized and characterized. [C(22)MIm][FSI], [C(18)MIm][FSI], and [C(22)MIm][TFSI] show smectic A(2) liquid crystalline mesophase. Single-crystal XRD revealed that [C(18)MIm][FSI] and [C(22)MIm][TFSI] show layered structures of low-polar and high-polar layers alternate with each other in the crystalline phase. It is suggested that perfluorinated sulfonylimide anions have relatively weak coulomb interactions with imidazolium headgroups, making them relatively difficult to form mesophase. (C) 2015 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.cplett.2015.04.003
• 作为试剂：
  描述：

  月桂酸 、 甘油 在 immobilized Candida antarctica Lipase B 、 1-methyl-3-octadecylimidazolium bis(trifluoromethylsulfonyl)amide 作用下， 以 叔丁醇 为溶剂， 生成 甘油单月桂酸酯 、 甘油三酯
  参考文献：
  名称：

  Highly selective biocatalytic synthesis of monoacylglycerides in sponge-like ionic liquids

  摘要：

  单酰基甘油通过在高选择性的海绵状离子液体中直接酯化生物催化合成（例如，在[C12mim][BF4]中可达100%的月桂酸单甘油酯）。

  DOI：

  10.1039/c6gc01969b

文献信息

• The Fluid-Mosaic Model, Homeoviscous Adaptation, and Ionic Liquids: Dramatic Lowering of the Melting Point by Side-Chain Unsaturation
  作者：Samuel M. Murray、Richard A. O'Brien、Kaila M. Mattson、Christopher Ceccarelli、Richard E. Sykora、Kevin N. West、James H. Davis

  DOI：10.1002/anie.200906169

  日期：2010.4.1

  Defying conventional wisdom: Ionic liquids (ILs) with long, unsaturated alkyl appendages (see top structure) defy established trends that link long ion‐bound alkyl groups to higher melting points. The new ILs are also less viscous than a saturated standard (see bottom structure) at the same temperature. These features parallel those that underpin homeoviscous adaptation in certain organisms and are

  违背传统常识：具有长且不饱和烷基附件的离子液体（IL）（参见顶部结构）无视已建立的趋势，这些趋势将长离子束缚的烷基与更高的熔点联系在一起。在相同温度下，新的离子液体的粘度也比饱和标准液（参见底部结构）低。这些特征与某些生物体内顺应性适应的特征平行，并间接支持类似流体马赛克的纳米级特征。
• Ionic liquid crystals based on 1-alkyl-3-methylimidazolium cations and perfluorinated sulfonylimide anions
  作者：Ting Li、Fei Xu、Wei Shi

  DOI：10.1016/j.cplett.2015.04.003

  日期：2015.5

  In contrast to the studies on ionic liquids based on perfluorinated sulfonylimide anions, their ionic liquid crystals were seldom reported. In the present study, four 1-alkyl-3-methylimidazolium perfluorinated sulfonylimide salts ([C(x)MIm][N(SO2RF)(2)], x = 18 and 22; R-F = F (FSI) and CF3(TFSI)) have been synthesized and characterized. [C(22)MIm][FSI], [C(18)MIm][FSI], and [C(22)MIm][TFSI] show smectic A(2) liquid crystalline mesophase. Single-crystal XRD revealed that [C(18)MIm][FSI] and [C(22)MIm][TFSI] show layered structures of low-polar and high-polar layers alternate with each other in the crystalline phase. It is suggested that perfluorinated sulfonylimide anions have relatively weak coulomb interactions with imidazolium headgroups, making them relatively difficult to form mesophase. (C) 2015 Elsevier B.V. All rights reserved.