6-(2',4'-dinitrobenzyl)-2,2'-bipyridine | 173470-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(2',4'-dinitrobenzyl)-2,2'-bipyridine
• 英文别名: 6-(2,4-dinitrobenzyl)-2,2'-bipyridine；6-(2,4-Dinitrobenzyl)-2,2'-bipyridin；6-(2',4'-Dinitrobenzyl)-2,2'-bipyridine；2-[(2,4-dinitrophenyl)methyl]-6-pyridin-2-ylpyridine
• CAS: 173470-96-7
• 化学式: C₁₇H₁₂N₄O₄
• 分子量: 336.307
• InChiKey: ARMLRUFIMZHTRJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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：

  6-(2',4'-dinitrobenzyl)-2,2'-bipyridine 在 乙醇-D1 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 168.0h， 生成 6-(2,4-dinitrobenzyl)-2,2'-bipyridine-d2
  参考文献：
  名称：

  Eichen, Yoav; Lehn, Jean-Marie; Scherl, Michael, Angewandte Chemie, 1995, vol. 107, # 22, p. 2753 - 2756

  摘要：

  DOI：
• 作为产物：
  描述：

  6-溴-2,2'-联吡啶 在 四(三苯基膦)钯 盐酸 、 硝酸 、 锌 作用下， 以 硫酸 为溶剂， 反应 6.0h， 生成 6-(2',4'-dinitrobenzyl)-2,2'-bipyridine
  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

• Packing-dependent photochromism: the case of photoinduced intramolecular proton transfer in 6-(2′,4′-dinitrobenzyl)-2,2′-bipyridine
  作者：Pance Naumov、Yuji Ohashi

  DOI：10.1107/s0108768104005506

  日期：2004.6.1

  photoinactive monoclinic beta-form) and with structures of related nitrobenzylpyridines to explain the relation between the structure and photochromism. The comparison of the reaction cavities around the reactive pyridyl-benzyl-nitro fragment among the polymorphs and related nitrobenzylpyridines revealed that a crucial factor for photochromic activity is the rotational freedom of the ortho-nitro group in

  从丙酮-甲醇溶液中获得了一种新的6-（2'，4'-二硝基苄基）-2,2'-联吡啶的光敏单斜晶型（γ型）。将晶体结构与先前报道的两种多晶型物的晶体结构（光活性正交α-型和光惰性单斜晶β-型）以及相关的硝基苄基吡啶的结构进行了比较，以解释结构与光致变色之间的关系。多晶型物和相关硝基苄基吡啶之间反应性吡啶基-苄基-硝基片段周围的反应腔的比较表明，光致变色活性的关键因素是其晶体中邻硝基的旋转自由度以及其从质子供体中的可及性和质子受体位点。
• Eichen, Yoav; Lehn, Jean-Marie; Scherl, Michael, Angewandte Chemie, 1995, vol. 107, # 22, p. 2753 - 2756
  作者：Eichen, Yoav、Lehn, Jean-Marie、Scherl, Michael、Haarer, Dietrich、Fischer, Jean、et al.

  DOI：——

  日期：——
• 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.