2-(2',4'-dinitrobenzyl)-1,10-phenanthroline | 163231-34-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 2-(2',4'-dinitrobenzyl)-1,10-phenanthroline
• 英文别名: 2-(2,4-dinitrobenzyl)-1,10-phenanthroline；2-[(2,4-dinitrophenyl)methyl]-1,10-phenanthroline
• CAS: 163231-34-3
• 化学式: C₁₉H₁₂N₄O₄
• 分子量: 360.329
• InChiKey: LZWIIITUKSRTJT-UHFFFAOYSA-N

物化性质

• 沸点：
  577.6±45.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2',4'-dinitrobenzyl)-1,10-phenanthroline 以 乙醇 为溶剂， 生成 2-[1-(2,4-Dinitro-phenyl)-meth-(Z)-ylidene]-1,2-dihydro-[1,10]phenanthroline
  参考文献：
  名称：

  Long-lived photoinduced proton transfer processes

  摘要：

  通过光诱导质子转移过程，辐照菲罗啉二硝基苄基化合物 3 生成一种长寿命同系物，其寿命是母体化合物 1a 的 5 × 103 倍。

  DOI：

  10.1039/c39950000713
• 作为产物：
  描述：

  苄基三苯基氯化膦 在 正丁基锂 、 硝酸 、 sodium carbonate 作用下， 以 硫酸 为溶剂， 反应 24.5h， 生成 2-(2',4'-dinitrobenzyl)-1,10-phenanthroline
  参考文献：
  名称：

  Proton-Transfer Processes in Well-Defined Media:  Experimental Investigation of Photoinduced and Thermal Proton-Transfer Processes in Single Crystals of 2-(2,4-Dinitrobenzyl)pyridine Derivatives

  摘要：

  A detailed spectroscopic study of photoinduced and thermally activated proton-transfer processes for a series of different crystals of 2-(2,4-dinitrobenzyl)pyridine derivatives has been performed. The quantitative analysis of ground- and excited-state activation barriers and preexponential factors in deuterated and nondeuterated crystals shows clearly that the observed photochromism is linked to a proton-transfer process. Furthermore, it is clearly seen that the supramolecular environment of the transferred proton participates in the proton-transfer process. These supramolecular effects control the relative rates and efficiencies of the observed proton-transfer processes in both the ground and excited state, yielding, at room temperature, photoproducts having lifetimes ranging between hours and weeks. At least two proton-accepting groups may be active in the abstraction of the proton from its relatively stable benzylic position. Additionally, low-temperature measurements of proton-transfer processes show that tunneling processes prevail at temperatures below 100 K only in the excited state. No evidence for tunneling could be found for ground-state processes.

  DOI：

  10.1021/jp9609242

文献信息

• Proton-Transfer Processes in Well-Defined Media:  Experimental Investigation of Photoinduced and Thermal Proton-Transfer Processes in Single Crystals of 2-(2,4-Dinitrobenzyl)pyridine Derivatives
  作者：Michael Scherl、Dietrich Haarer、Jean Fischer、André DeCian、Jean-Marie Lehn、Yoav Eichen

  DOI：10.1021/jp9609242

  日期：1996.1.1

  A detailed spectroscopic study of photoinduced and thermally activated proton-transfer processes for a series of different crystals of 2-(2,4-dinitrobenzyl)pyridine derivatives has been performed. The quantitative analysis of ground- and excited-state activation barriers and preexponential factors in deuterated and nondeuterated crystals shows clearly that the observed photochromism is linked to a proton-transfer process. Furthermore, it is clearly seen that the supramolecular environment of the transferred proton participates in the proton-transfer process. These supramolecular effects control the relative rates and efficiencies of the observed proton-transfer processes in both the ground and excited state, yielding, at room temperature, photoproducts having lifetimes ranging between hours and weeks. At least two proton-accepting groups may be active in the abstraction of the proton from its relatively stable benzylic position. Additionally, low-temperature measurements of proton-transfer processes show that tunneling processes prevail at temperatures below 100 K only in the excited state. No evidence for tunneling could be found for ground-state processes.
• Long-lived photoinduced proton transfer processes
  作者：Yoav Eichen、Jean-Marie Lehn、Michael Scherl、Dietrich Haarer、Roger Casalegno、Anne Corval、Karla Kuldova、H. Peter Trommsdorff

  DOI：10.1039/c39950000713

  日期：——

  Irradiation of the phenanthroline–dinitrobenzyl compound 3 generates, via a photoinduced proton transfer process, a long-lived tautomer having a lifetime about 5 × 103 times longer than that of the parent compound 1a.

  通过光诱导质子转移过程，辐照菲罗啉二硝基苄基化合物 3 生成一种长寿命同系物，其寿命是母体化合物 1a 的 5 × 103 倍。