N²,N⁶-di(4-nitrophenyl)pyridine-2,6-dicarboxamide | 313516-94-8

• 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: N²,N⁶-di(4-nitrophenyl)pyridine-2,6-dicarboxamide
• 英文别名: N,N'-bis(4-nitrophenyl)pyridine-2,6-dicarboxamide；2-N,6-N-bis(4-nitrophenyl)pyridine-2,6-dicarboxamide
• CAS: 313516-94-8
• 化学式: C₁₉H₁₃N₅O₆
• mdl: MFCD00989812
• 分子量: 407.342
• InChiKey: MGVCXKGITHCUPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  N²,N⁶-di(4-nitrophenyl)pyridine-2,6-dicarboxamide 以 氘代氯仿 为溶剂， 反应 48.0h， 生成
  参考文献：
  名称：

  Chemical Mustard Containment Using Simple Palladium Pincer Complexes: The Influence of Molecular Walls

  摘要：

  Six amide-based NNN palladium(II) pincer complexes Pd(L)(CH3CN) were synthesized, characterized, and examined for binding the sulfur mustard surrogate, 2-chloroethyl ethyl sulfide (CEES). The complexes all bind readily with CEES as shown by 'H NMR spectroscopy in CDCl3. The influence of parasubstituents on the two amide phenyl appendages was explored as well as the effect of replacing the phenyl groups with larger aromatic rings, 1-naphthalene and 9-anthracene. While variations of the parasubstituents had only a slight influence on the binding affinities, incorporation of larger aromatic rings resulted in a significant size-related increase in binding, possibly due to increasing steric and electronic interactions. In crystal structures of three CEES-bound complexes, the mustard binds through the sulfur atom and lies along the aromatic walls of the side appendages approximately perpendicular to the pincer plane, with increasingly better alignment progressing from phenyl to 1-naphthalene to 9-anthracene.

  DOI：

  10.1021/ja408770u
• 作为产物：
  描述：

  吡啶-2,6-二甲酸 在 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 N²,N⁶-di(4-nitrophenyl)pyridine-2,6-dicarboxamide
  参考文献：
  名称：

  吡啶-2,6-二甲酰胺和呋喃-2,5-二甲酰胺衍生物的合成及结构表征

  摘要：

  基于吡啶-2-6-和呋喃-2,5-二甲酰胺支架的衍生物揭示了许多化学性质和生物活性。这一事实使它们成为超分子和配位化学以及发现新的药理活性化合物方面令人兴奋的研究课题。本工作旨在通过适当的酰氯和芳香酰胺的缩合反应获得一系列对称的吡啶-2-6-和呋喃-2,5-二甲酰胺。核磁共振波谱证实了合成的成功。我们解析了七种化合物的晶体结构；二吡啶和五呋喃衍生物。根据我们的晶体学研究，我们能够表明所研究晶体的超分子特征。此外，赫什菲尔德表面分析使我们能够计算二甲酰胺晶体中分子间接触的分布。

  DOI：

  10.3390/molecules27061819

文献信息

• Dianilides of dipicolinic acid function as synthetic chloride channels
  作者：Carl R. Yamnitz、Saeedeh Negin、I. Alexandru Carasel、Rudolph K. Winter、George W. Gokel

  DOI：10.1039/b924812a

  日期：——

  We report that N2,N6-bis(4-nitrophenyl)pyridine-2,6-dicarboxamide, which is related to known isophthalic acid dianilides, transports Cl− ions through phospholipid bilayer membranes and shows clear evidence of channel activity.

  我们报告说，N2,N6-双（4-硝基苯基）吡啶-2,6-二甲酰胺与已知的间苯二甲酸二酰二胺相关，可通过磷脂双层膜转运 Cl- 离子，并显示出明确的通道活性证据。
• 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.
• N,N′-Bis(aryl)pyridine-2,6-dicarboxamide complexes of ruthenium: Synthesis, structure and redox properties
  作者：Moutusi Dasgupta、Sumon Nag、Gopal Das、Munirathinam Nethaji、Samaresh Bhattacharya

  DOI：10.1016/j.poly.2007.08.042

  日期：2008.1

  Reaction of five N,N'-bis(aryl)pyridine-2,6-dicarboxamides (H2L-R, where H-2 denotes the two acidic protons and R (R = OCH3, CH3, H, Cl and NO2) the para substituent in the aryl fragment) with [Ru(trpy)Cl-3](trpy = 2,2',2"-terpyridine) in refluxing ethanol in the presence of a base (NEW affords a group of complexes of the type [Ru-II(trpy)(L-R)], each of which contains an amide ligand coordinated to the metal center as a dianionic tridentate N,N,N-donor along with a terpyridine ligand. Structure of the [Ru-II(trpy)(L-Cl)] complex has been determined by X-ray crystallography. All the Ru(II) complexes are diamagnetic, and show characteristic H-1 NMR signals and intense MLCT transitions in the visible region. Cyclic voltammetry on the [Ru-II(trpy)(L-R)] complexes shows a Ru(II)-Ru(III) oxidation within 0.16-0.33 V versus SCE. An oxidation of the coordinated amide ligand is also observed within 0.94-1.33 V versus SCE and a reduction of coordinated terpyridine ligand within -1.10 to -1.15 V versus SCE. Constant potential coulometric oxidation of the [Ru-II(trpy)(L-R)] complexes produces the corresponding [Ru-II(trpy)(L-R)](+) complexes, which have been isolated as the perchlorate salts. Structure of the [Ru-III(trpy)(L-CH3)ClO4 complex has been determined by X-ray crystallography. All the Ru(Ill) complexes are one-electron paramagnetic, and show anisotropic ESR spectra at 77 K and intense LMCT transitions in the visible region. A weak ligand-field band has also been shown by all the [Ru-III(trpy)(L-R)]ClO4 complexes near 1600 nm. (C) 2007 Elsevier Ltd. All rights reserved.
• Chemical Mustard Containment Using Simple Palladium Pincer Complexes: The Influence of Molecular Walls
  作者：Qi-Qiang Wang、Rowshan Ara Begum、Victor W. Day、Kristin Bowman-James

  DOI：10.1021/ja408770u

  日期：2013.11.13

  Six amide-based NNN palladium(II) pincer complexes Pd(L)(CH3CN) were synthesized, characterized, and examined for binding the sulfur mustard surrogate, 2-chloroethyl ethyl sulfide (CEES). The complexes all bind readily with CEES as shown by 'H NMR spectroscopy in CDCl3. The influence of parasubstituents on the two amide phenyl appendages was explored as well as the effect of replacing the phenyl groups with larger aromatic rings, 1-naphthalene and 9-anthracene. While variations of the parasubstituents had only a slight influence on the binding affinities, incorporation of larger aromatic rings resulted in a significant size-related increase in binding, possibly due to increasing steric and electronic interactions. In crystal structures of three CEES-bound complexes, the mustard binds through the sulfur atom and lies along the aromatic walls of the side appendages approximately perpendicular to the pincer plane, with increasingly better alignment progressing from phenyl to 1-naphthalene to 9-anthracene.
• Synthesis and Structural Characterization of Pyridine-2,6-dicarboxamide and Furan-2,5-dicarboxamide Derivatives
  作者：Anna Puckowska、Magdalena Gawel、Marlena Komorowska、Pawel Drozdzal、Aleksandra Arning、Damian Pawelski、Krzysztof Brzezinski、Marta E. Plonska-Brzezinska

  DOI：10.3390/molecules27061819

  日期：——

  condensation reaction of the appropriate acyl chlorides and aromatic amides. Successful syntheses were confirmed with NMR spectroscopy. We solved their crystal structures for seven compounds; two pyridine and five furan derivatives. Based on our crystallographic studies, we were able to indicate supramolecular features of the crystals under investigation. Additionally, Hirshfeld surface analysis allowed us

  基于吡啶-2-6-和呋喃-2,5-二甲酰胺支架的衍生物揭示了许多化学性质和生物活性。这一事实使它们成为超分子和配位化学以及发现新的药理活性化合物方面令人兴奋的研究课题。本工作旨在通过适当的酰氯和芳香酰胺的缩合反应获得一系列对称的吡啶-2-6-和呋喃-2,5-二甲酰胺。核磁共振波谱证实了合成的成功。我们解析了七种化合物的晶体结构；二吡啶和五呋喃衍生物。根据我们的晶体学研究，我们能够表明所研究晶体的超分子特征。此外，赫什菲尔德表面分析使我们能够计算二甲酰胺晶体中分子间接触的分布。