3-methyl-1-sulfoimidazolium trifluoroacetate | 1380315-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-1-sulfoimidazolium trifluoroacetate
• CAS: 1380315-10-5
• 化学式: C₂F₃O₂*C₄H₇N₂O₃S
• 分子量: 276.193
• InChiKey: JNDMGBIQEZMCQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.74
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  103.31
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  3-methyl-1-sulfonic acid imidazolium chloride 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 24.0h， 以89%的产率得到3-methyl-1-sulfoimidazolium trifluoroacetate
  参考文献：
  名称：

  Hydration of alkynes using Brönsted acidic ionic liquids in the absence of Nobel metal catalyst/H2SO4

  摘要：

  In this study, a variety of imidazole based sulfonic acid group functionalized Bronsted acidic ionic liquids (BAILs) were synthesized. BAILs have been successfully developed as task specific ionic liquids for hydration of alkynes under mild conditions to give high yields of ketones as a selective product. Acidity of BAILs was determined using volumetric titration and UV-visible spectroscopic methods. The Hammett acidity order and acid value of BAILS correlate well with the activity order observed for most of the BAILs in the hydration reaction of phenylacetylene. Theoretical studies demonstrate that hydrogen bonding plays a key role in tuning the acidity of BAILs. Density function theory calculations are also able to explain the difference in activity observed in these BAILS. The activity of ionic liquids was theoretically studied by computing the activation energy for the hydration reaction. Recycling experiments suggest that these novel BAILS can be reused without significant loss in activity. BAILS are simple and easy to prepare and exhibit excellent activity toward the hydration of a variety of alkynes to ketones. Moreover, the reaction involving BAILS does not involve heavy metal catalysts or H2SO4. Novel BAILs offer several attractive features such as sustainable synthetic route, low cost, moisture stability, high yields, and recyclability. (c) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcata.2012.04.010