1,3-bis(2-bromo-imidazol-1-yl)benzene | 1374149-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1,3-bis(2-bromo-imidazol-1-yl)benzene
• 英文别名: 1,3-bis(2-bromoimidazol-1-yl)benzene；2-Bromo-1-[3-(2-bromoimidazol-1-yl)phenyl]imidazole
• CAS: 1374149-84-4
• 化学式: C₁₂H₈Br₂N₄
• 分子量: 368.03
• InChiKey: LVJQIRYQCDMVIO-UHFFFAOYSA-N

物化性质

• 沸点：
  562.7±60.0 °C(predicted)
• 密度：
  1.87±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(2-bromo-imidazol-1-yl)benzene 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 24.0h， 以48%的产率得到1,3-bis(2-bromo-3-methylimidazolium)phenyl bis(trifluoromethanesulfonate)
  参考文献：
  名称：

  Isothermal Calorimetric Titrations on Charge-Assisted Halogen Bonds: Role of Entropy, Counterions, Solvent, and Temperature

  摘要：

  We have conducted isothermal calorimetric titrations to investigate the halogen-bond strength of cationic bidentate halogen-bond donors toward halides, using bis(iodoimidazolium) compounds as probes. These data are intended to aid the rational design of halogen-bond donors as well as the development of halogen-bond-based applications in solution. In all cases examined, the entropic contribution to the overall free energy of binding was found to be very important. The binding affinities showed little dependency on the weakly coordinating counteranions of the halogen-bond donors but became slightly stronger with higher temperatures. We also found a marked influence of different solvents on the interaction strength. The highest binding constant detected in this study was 3.3 x 10(6) M-1.

  DOI：

  10.1021/ja2119207
• 作为产物：
  描述：

  1,3-二(1H-咪唑-1-基)苯 在 正丁基锂 、 四溴化碳 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以59%的产率得到1,3-bis(2-bromo-imidazol-1-yl)benzene
  参考文献：
  名称：

  NMR Quantification of Halogen-Bonding Ability To Evaluate Catalyst Activity

  摘要：

  Quantification of halogen-bonding abilities is described for a series of benzimidazolium-, imidazolium- and bis(imidazolium) halogen-bond donors (XBDs) using P-31 NMR spectroscopy. The measured Delta delta(P-31) values correlate with calculated activation free energy Delta G(double dagger) and catalytic activity for a Friedel-Crafts indole addition. This rapid method also serves as a sensitive indicator for Bronsted acid impurities.

  DOI：

  10.1021/acs.orglett.0c02427

文献信息

• Cationic Multidentate Halogen-Bond Donors in Halide Abstraction Organocatalysis: Catalyst Optimization by Preorganization
  作者：Stefan H. Jungbauer、Stefan M. Huber

  DOI：10.1021/jacs.5b07863

  日期：2015.9.23

  show that the catalytic activity is based on halogen bonding using, e.g., the chlorinated derivatives as reference compounds. On the basis of these studies, halobenzimidazolium organocatalysts were then investigated. Monodentate compounds featured the same trends as the corresponding imidazolium analogues but showed a stronger catalytic activity. In order to prepare bidentate versions which are preorganized

  与在有机催化中牢固建立的氢键相反，卤素键在该领域的应用仍然很少。在此，我们首次展示了阳离子卤素键供体在卤化物提取反应中的催化应用。首先，系统地测试了基于卤代吡啶鎓、卤咪唑鎓和卤化 1,2,3-三唑鎓的催化剂。与吡啶鎓化合物相比，咪唑鎓和三唑鎓盐均显示出有希望的效力。对于基于卤代咪唑鎓的有机催化剂，我们可以证明催化活性基于卤素键合，例如使用氯化衍生物作为参考化合物。在这些研究的基础上，研究了卤代苯并咪唑鎓有机催化剂。单齿化合物与相应的咪唑鎓类似物具有相同的趋势，但表现出更强的催化活性。为了制备预先组织用于阴离子结合的二齿形式，合成了一类新的刚性双（卤代苯并咪唑鎓）化合物并对其进行了结构表征。相应的顺式异构体显示出前所未有的催化效力，可以低至 0.5 mol% 用于 1-氯异色满与甲硅烷基烯醇醚的基准反应。计算证实顺式异构体可能以双齿方式与氯化物结合。各自的反异构体活性较低并且以单齿方式结合卤