1-(3-(imidazol-1-yl)phenyl)-2-iodoimidazole | 1374149-80-0

• 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-(3-(imidazol-1-yl)phenyl)-2-iodoimidazole
• 英文别名: 1-(3-(1H-imidazol-1-yl)phenyl)-2-iodo-1H-imidazole
• CAS: 1374149-80-0
• 化学式: C₁₂H₉IN₄
• 分子量: 336.135
• InChiKey: WVDGAFRHNTZPPP-UHFFFAOYSA-N

物化性质

• 沸点：
  524.6±52.0 °C(predicted)
• 密度：
  1.77±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.66
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  35.64
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(3-(imidazol-1-yl)phenyl)-2-iodoimidazole 、 n-octyl triflate 以 二氯甲烷 为溶剂， 以75%的产率得到2-iodo-3-octyl-1-(3-(3-octyl-1H-imidazol-3-ium-1-yl)phenyl)-1H-imidazol-3-ium bis(trifluoromethanesulfonate)
  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
• 作为产物：
  描述：

  1,3-二(1H-咪唑-1-基)苯 在 正丁基锂 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以48%的产率得到1-(3-(imidazol-1-yl)phenyl)-2-iodoimidazole
  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

• Isothermal Calorimetric Titrations on Charge-Assisted Halogen Bonds: Role of Entropy, Counterions, Solvent, and Temperature
  作者：Sebastian M. Walter、Florian Kniep、Laxmidhar Rout、Franz P. Schmidtchen、Eberhardt Herdtweck、Stefan M. Huber

  DOI：10.1021/ja2119207

  日期：2012.5.23

  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.