N,N'-bis(2-nitrophenyl)pyridine-2,6-dicarboxamide | 312941-88-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(2-nitrophenyl)pyridine-2,6-dicarboxamide
• 英文别名: N2,N6-Bis(2-nitrophenyl)pyridine-2,6-dicarboxamide；2-N,6-N-bis(2-nitrophenyl)pyridine-2,6-dicarboxamide
• CAS: 312941-88-1
• 化学式: C₁₉H₁₃N₅O₆
• mdl: MFCD00805663
• 分子量: 407.342
• InChiKey: GLGUBHCTGYZBNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  163
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2-nitrophenyl)pyridine-2,6-dicarboxamide 在 盐酸 、 铁粉 作用下， 以 甲醇 为溶剂， 以76 %的产率得到N²,N⁶-bis(2-aminophenyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  仿生设计的不带电双极螺旋支架实现高效固态质子传导

  摘要：

  在从不同极性的溶剂中获得的两种不同固体形式中观察到基于吡啶-2,6-二甲酰胺的螺旋支架的立体发散堆积。在黄色形式中观察到有效的固态质子传导，其具有纯手性分子排列，分子间更接近，并且极性残基的空间排列。

  DOI：

  10.1002/chem.202300019
• 作为产物：
  描述：

  2,6-氯甲酰吡啶 、 2-硝基苯胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以89%的产率得到N,N'-bis(2-nitrophenyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors

  摘要：

  The synthesis of simple, chromogenic pyridine-2,6-dicarboxylic acid amides, derivatives of isomeric nitroanilines and aminonitrophenols, and their ion binding properties are described. The ligands' response to ionic species was examined by naked eye and was studied with the use of UV-vis spectroscopy in DMSO and its mixture with water. The effect of the localisation and the type of the substituents in aromatic rings were discussed. H-1 NMR experiments were carried out to probe the mechanism of anion recognition, i.e. complexation via hydrogen bond formation versus ligand deprotonation. A selective response of N,N'-bis(2-hydroxy-4-nitrophenyl)pyridine-2,6-dicarboxamide (L5) towards dihydrogen phosphate was found in both DMSO and DMSO-water (95: 5) solvent mixture. The structure of N,N'-bis(2-hydroxy-5-nitrophenyl)pyridine-2,6-dicarboxamide (L4) was confirmed by X-ray crystallography.

  DOI：

  10.1080/10610278.2012.695789

文献信息

• Chromogenic amides of pyridine-2,6-dicarboxylic acid as anion receptors
  作者：Ewa Wagner-Wysiecka、Jarosław Chojnacki

  DOI：10.1080/10610278.2012.695789

  日期：2012.9.1

  The synthesis of simple, chromogenic pyridine-2,6-dicarboxylic acid amides, derivatives of isomeric nitroanilines and aminonitrophenols, and their ion binding properties are described. The ligands' response to ionic species was examined by naked eye and was studied with the use of UV-vis spectroscopy in DMSO and its mixture with water. The effect of the localisation and the type of the substituents in aromatic rings were discussed. H-1 NMR experiments were carried out to probe the mechanism of anion recognition, i.e. complexation via hydrogen bond formation versus ligand deprotonation. A selective response of N,N'-bis(2-hydroxy-4-nitrophenyl)pyridine-2,6-dicarboxamide (L5) towards dihydrogen phosphate was found in both DMSO and DMSO-water (95: 5) solvent mixture. The structure of N,N'-bis(2-hydroxy-5-nitrophenyl)pyridine-2,6-dicarboxamide (L4) was confirmed by X-ray crystallography.
• Bioinspired Design of an Uncharged Ambipolar Helical Scaffold To Achieve Efficient Solid‐State Proton Conduction
  作者：Himanshu Aggarwal、Pradip A. Gaikwad、Anjali Dahat、Swapnendu Narayan Ghosh、Palak Mehra、Amit Paul、Santanu Talukder、Aasheesh Srivastava

  DOI：10.1002/chem.202300019

  日期：——

  Stereo-divergent packing of helical scaffolds based on pyridine-2,6-dicarboxamide is observed in two different solid forms obtained from solvents of different polarity. Efficient solid-state proton conduction is observed in the yellow form, which has a homochiral molecular arrangement with closer intermolecular proximity, and spatial alignment of polar residues.

  在从不同极性的溶剂中获得的两种不同固体形式中观察到基于吡啶-2,6-二甲酰胺的螺旋支架的立体发散堆积。在黄色形式中观察到有效的固态质子传导，其具有纯手性分子排列，分子间更接近，并且极性残基的空间排列。