6,6'-(2,2'-bipyridine-4,4'-diyl)bis(1,3,5-triazine-2,4-diamine) | 1268344-20-2

• 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: 6,6'-(2,2'-bipyridine-4,4'-diyl)bis(1,3,5-triazine-2,4-diamine)
• 英文别名: 6-[2-[4-(4,6-Diamino-1,3,5-triazin-2-yl)pyridin-2-yl]pyridin-4-yl]-1,3,5-triazine-2,4-diamine
• CAS: 1268344-20-2
• 化学式: C₁₆H₁₄N₁₂
• 分子量: 374.368
• InChiKey: KQFPIILQQFPEDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  207
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  二聚氰胺 、 4,4'-二氰基-2,2'-二嘧啶 在 potassium hydroxide 作用下， 以 甲乙醚 为溶剂， 反应 12.0h， 以85%的产率得到6,6'-(2,2'-bipyridine-4,4'-diyl)bis(1,3,5-triazine-2,4-diamine)
  参考文献：
  名称：

  Syntheses and Structures of Isomeric Diaminotriazinyl-Substituted 2,2′-Bipyridines and 1,10-Phenanthrolines

  摘要：

  Isomeric 2,2'-bipyridines 4a-6a and 1,10-phenanthrolines 7a-9a with two diaminotriazinyl (DAT) substituents were synthesized to explore their dual ability to direct association by the chelation of metals and the characteristic hydrogen bonding of DAT groups. Crystals of compounds 4a-6a and 7a-9a were grown under diverse conditions, and their structures were solved by X-ray crystallography. Analysis revealed multiple shared features analogous to those observed in the structures of simpler DAT-substituted pyridines 1-3. For example, the bipyridines and phenanthrolines favor flattened conformations except in the cases of compounds 8a and 9a, where the patterns of substitution prevent the DAT groups from lying in the plane of the phenanthroline core. As expected, the DAT groups form approximately coplanar hydrogen bonds according to standard motifs I-III, which play a key role in directing molecular organization. However, the structures of simple pyridines 1-3, which favor efficiently packed chains and sheets, differ predictably from those of bipyridines 4a-6a and phenanthrolines 7a-9a in two ways: (1) The larger number of DAT groups in compounds 4a-9a typically leads to complex three-dimensional networks held together by a larger number of hydrogen bonds per molecule, and (2) the need to respect multiple directional interactions prevents compounds 4a-9a from forming closely packed structures, and significant quantities of guests are included. Together, these observations confirm the effectiveness of incorporating special groups such as DAT within more complex molecular structures to control association according to reliable patterns. Bipyridines 4a-6a and phenanthrolines 7a-9a promise to be particularly rich sources of new supramolecular chemistry because they have well-defined molecular topologies and a dual ability to direct association by chelating metals and by engaging in multiple hydrogen bonds according to reliable patterns.

  DOI：

  10.1021/jo102191n

文献信息

• Syntheses and Structures of Isomeric Diaminotriazinyl-Substituted 2,2′-Bipyridines and 1,10-Phenanthrolines
  作者：Adam Duong、Thierry Maris、Olivier Lebel、James D. Wuest

  DOI：10.1021/jo102191n

  日期：2011.3.4

  Isomeric 2,2'-bipyridines 4a-6a and 1,10-phenanthrolines 7a-9a with two diaminotriazinyl (DAT) substituents were synthesized to explore their dual ability to direct association by the chelation of metals and the characteristic hydrogen bonding of DAT groups. Crystals of compounds 4a-6a and 7a-9a were grown under diverse conditions, and their structures were solved by X-ray crystallography. Analysis revealed multiple shared features analogous to those observed in the structures of simpler DAT-substituted pyridines 1-3. For example, the bipyridines and phenanthrolines favor flattened conformations except in the cases of compounds 8a and 9a, where the patterns of substitution prevent the DAT groups from lying in the plane of the phenanthroline core. As expected, the DAT groups form approximately coplanar hydrogen bonds according to standard motifs I-III, which play a key role in directing molecular organization. However, the structures of simple pyridines 1-3, which favor efficiently packed chains and sheets, differ predictably from those of bipyridines 4a-6a and phenanthrolines 7a-9a in two ways: (1) The larger number of DAT groups in compounds 4a-9a typically leads to complex three-dimensional networks held together by a larger number of hydrogen bonds per molecule, and (2) the need to respect multiple directional interactions prevents compounds 4a-9a from forming closely packed structures, and significant quantities of guests are included. Together, these observations confirm the effectiveness of incorporating special groups such as DAT within more complex molecular structures to control association according to reliable patterns. Bipyridines 4a-6a and phenanthrolines 7a-9a promise to be particularly rich sources of new supramolecular chemistry because they have well-defined molecular topologies and a dual ability to direct association by chelating metals and by engaging in multiple hydrogen bonds according to reliable patterns.