N,N′-[(1,4-phenylene)bis(methylene)]bis(pyridine-4-carboxamide) | 548451-53-2

• 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: N,N′-[(1,4-phenylene)bis(methylene)]bis(pyridine-4-carboxamide)
• 英文别名: N,N'-[1,4-phenylenebis-(methylene)]bis-4-pyridinecarboxamide；N,N'-[(1,4-phenylene)bis(methylene)]bis(pyridine-4-carboxamide)；H₂pbbp；H₂H₂pbbp；N-[(4-{[(Pyridin-4-YL)formamido]methyl}phenyl)methyl]pyridine-4-carboxamide；N-[[4-[(pyridine-4-carbonylamino)methyl]phenyl]methyl]pyridine-4-carboxamide
• CAS: 548451-53-2
• 化学式: C₂₀H₁₈N₄O₂
• mdl: MFCD03403300
• 分子量: 346.389
• InChiKey: JYPVPHWDJOVEBV-UHFFFAOYSA-N

物化性质

• 熔点：
  197-199 °C
• 沸点：
  720.9±60.0 °C(Predicted)
• 密度：
  1.246±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  84
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N′-[(1,4-phenylene)bis(methylene)]bis(pyridine-4-carboxamide) 、 以 甲醇 为溶剂， 反应 24.0h， 以91%的产率得到
  参考文献：
  名称：

  具有Cp * Rh构建基块的分子三叶形结和双三叶形结的无模板自组装。

  摘要：

  理解和控制自组装结构的拓扑在超分子化学中起着基本作用。在这里，我们描述了通过四个不同的刚性和柔性配体的无模板自组装来制备一系列具有Cp * Rh构建基块的四核金属矩形和六核三叶结。三叶结与相应的大环之间的转化可以利用集中效应来诱导。值得注意的是，六核三叶结5进一步组装，通过酰胺氧原子与次要金属离子Na + / K +的配位提供了[12 + 1]异核双三叶结（5a / 5b / 5c / 5d）的罕见例子。 / Ca2 + / Cd2 +。合成结果得到单晶X射线衍射分析的支持。

  DOI：

  10.1002/chem.202000525
• 作为产物：
  描述：

  1,4-苯二甲胺 、 氯化异氰盐酸盐 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以86%的产率得到N,N′-[(1,4-phenylene)bis(methylene)]bis(pyridine-4-carboxamide)
  参考文献：
  名称：

  [2]连环烷中的构象溶剂同形

  摘要：

  柔性吡啶附加配体（L1）与4,4'-联吡啶（L2）和顺式保护的Pd（II）单元Pd（L'）（NO 3）2的组合在水中产生浓度依赖性相应的[2] catenanes [Pd 2（L'）2（L1）（L2）] 2（NO 3）8及其组成的大环[Pd 2（L'）2（L1）（L2）]的平衡混合物NO 3）4。该顺所用的-保护单元（L'）是乙二胺（en），四甲基乙二胺（tmeda），2,2'-联吡啶（bpy）和1,10-菲咯啉（phen）。在[Pd 2（2,2'-bpy）2（L1）（）的情况下，通过缓慢蒸发其CH 3 CN / H 2 O（1：1）溶液而使[2]邻苯二酚结晶可得到单晶形式。[Pd 2（phen）2（L1）（L2）] 2（NO 3）8的情况下，L 2）] 2（NO 3）8和两种伴随的结晶形式（溶剂化物）。非共价相互作用（例如N–H··O，C–H··O和C–H···π接触以及π···π堆积）促进了[2]环戊烷的形成。[Pd

  DOI：

  10.1021/acs.cgd.0c00421

文献信息

• Five zinc supramolecular assemblies constructed from flexible bispyridinecarboxamide and a series of substituted isophthalates: Synthesis and characterization
  作者：Zhehui Weng、Xiaohua Zhou、Jie Ling、Pengzhi Xiang、Yao Huang、Haidong Ju、Shengchun Chen、Zhihui Zhang

  DOI：10.1016/j.jssc.2021.122660

  日期：2022.1

  Five new coordination assemblies of substituted zinc(II) isophthalates and H2pbbp H2pbbp ​= ​N,N′-[(1,4-phenylene)bis(methylene)]bis(pyridine-4-carboxamide)} linkers, namely, [Zn(pbbp)(Fip)]n, 1, [Zn(pbbp)(Nip)∙H2O]n, 2, [Zn(pbbp)(Mip)∙H2O]n, 3, [Zn(pbbp)(Bip)·H2O]n, 4, [Zn(pbbp)(TM)(H2O)·H2O]n, 5 have been synthesized under hydrothermal conditions. Single-crystal X-ray diffraction analysis reveals

  取代的锌的五个新的协调组件（II）间苯二甲酸酯和H 2 PBBP H 2 PBBP = Ñ，Ñ ' - [（1,4-亚苯基）二（亚甲基）]二（吡啶-4-甲酰胺）}接头, 即 [Zn(pbbp)(Fip)] n , 1 , [Zn(pbbp)(Nip)∙H 2 O] n , 2 , [Zn(pbbp)(Mip)∙H 2 O] n , 3 , [Zn(pbbp)(Bip)·H 2 O] n , 4 , [Zn(pbbp)(TM)(H 2 O)·H 2 O] n , 5是在水热条件下合成的。单晶 X 射线衍射分析显示化合物1-5表现出二维层状结构。由于强氢键，化合物1-4中的层状结构进一步扩展为三维超分子网络。还研究了这些化合物的热稳定性、粉末 X 射线衍射、红外光谱和发光特性。
• Coordination Assembly of Zn^II/Cd^II Terephthalate with Bis-Pyridinecarboxamide Tectons: Establishing Net Entanglements from [3 + 3] Interpenetration to High-Connected Self-Penetration
  作者：Zhi-Hui Zhang、Sheng-Chun Chen、Ming-Yang He、Qun Chen、Miao Du

  DOI：10.1021/cg4000445

  日期：2013.3.6

  Four polymeric d(10) metal terephthalate complexes incorporating bis-pyridinecarboxamide building blocks were prepared to explore the effect of the central metal ion or the fluorine substituent of the ligand on the topology and entanglement of coordination networks. The combination of Zn-II terephthalate with a fluorinated ligand leads to a noninterpenetrated coordination layer with honeycomb (hcb) topology for complex 1. Interestingly, the other three materials display the unusual entangling coordination networks. For 2, the reaction of zinc terephthalate with nonfluorinated ligand affords three-dimensional diamond (dia) architecture of [3 + 3] interpenetration, while the Cd-II terephthalate complexes 3 and 4 with the two types of bis-pyridinecarboxamide tectons show the isostructural self-penetrating framework with unique 8-connected (4(17).6(11)) topology.
• Syntheses and studies of flexible amide ligands: a toolkit for studying metallo-supramolecular assemblies for anion binding
  作者：Christopher J. Sumby、Lyall R. Hanton

  DOI：10.1016/j.tet.2009.04.031

  日期：2009.6

  The syntheses of seven flexible bidentate bis-pyridyl diamide and four monodentate pyridyl amide ligands containing central amide units are described. The bis-pyridyl ligands were prepared in one step from commercially available compounds in moderate to good yield. These compounds all possess external metal coordinating pyridyl groups and internal amide functionalities, with the potential to bind anions. Crystal structures of six of the bis-pyridyl diamide ligands are described. The four compounds with xylene cores N,N'-[1,3-phenylenebis(methylene)]bis-3-pyridinecarboxamide 1, N,N'-[1,3-phenylenebis(methylene)]bis-4-pyridinecarboxamide 2, N,N'-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 3 and N,N'-[1,4-phenylenebis(methylene)]bis-4-pyridinecarboxamide 4 crystallize with extensive amide N-H center dot center dot center dot O=C hydrogen bonding between the diamide compounds, giving rise to two and three dimensional hydrogen bonded networks. N,N'-Bis(3-pyridylmethyl)benzene-1,3-dicarboxamide 5, the only compound with the amide groups directly attached to a central benzene core, was not able to be crystallised. N,N'-2,6-Bis(3-pyridylmethyl)pyridine dicarboxamide 6 and N,N'-2,6-bis(4-pyridylmethyl)pyridine dicarboxamide 7 have a mismatch of hydrogen bond donor and acceptor regions preventing ready involvement of the amide NH groups in network formation. For comparison we also prepared compounds N,N'-2'-propyl-6-(3-pyridylmethyl)pyrid me dicarboxamide 10 and N,N'-2'-propyl-6-(4-pyridylmethyl)pyridine dicarboxamide 11 with two amide groups but only the one external donor pyridyl moiety, and compounds N-6-[(3-pyridylmethyl amino)carbonyl]-2-pyridinecarboxylic acid methyl ester 8 and N-6-[(4-pyridylmethylamino)-carbonyl] -2-pyridinecarboxylic acid methyl ester 9, which have only the one amide. (C) 2009 Elsevier Ltd. All rights reserved.
• Conformational Solvatomorphism in a [2]Catenane
  作者：Shobhana Krishnaswamy、Soumyakanta Prusty、Daniel Chartrand、Garry S. Hanan、Dillip K. Chand

  DOI：10.1021/acs.cgd.0c00421

  日期：2020.9.2

  ligands and phen units in the macrocycles and may thus be termed conformational solvatomorphs. The molecular packing in all the structures was found to be driven by intermolecular π···π stacking interactions between the aromatic rings in their cis-protected Pd(II) units. However, because of the awkward shape of the molecules, the closest 2,2′-bpy and phen units in all the structures overlap differently

  柔性吡啶附加配体（L1）与4,4'-联吡啶（L2）和顺式保护的Pd（II）单元Pd（L'）（NO 3）2的组合在水中产生浓度依赖性相应的[2] catenanes [Pd 2（L'）2（L1）（L2）] 2（NO 3）8及其组成的大环[Pd 2（L'）2（L1）（L2）]的平衡混合物NO 3）4。该顺所用的-保护单元（L'）是乙二胺（en），四甲基乙二胺（tmeda），2,2'-联吡啶（bpy）和1,10-菲咯啉（phen）。在[Pd 2（2,2'-bpy）2（L1）（）的情况下，通过缓慢蒸发其CH 3 CN / H 2 O（1：1）溶液而使[2]邻苯二酚结晶可得到单晶形式。[Pd 2（phen）2（L1）（L2）] 2（NO 3）8的情况下，L 2）] 2（NO 3）8和两种伴随的结晶形式（溶剂化物）。非共价相互作用（例如N–H··O，C–H··O和C–H···π接触以及π···π堆积）促进了[2]环戊烷的形成。[Pd
• Template‐Free Self‐Assembly of Molecular Trefoil Knots and Double Trefoil Knots Featuring Cp*Rh Building Blocks
  作者：Wei‐Long Shan、Xiang Gao、Yue‐Jian Lin、Guo‐Xin Jin

  DOI：10.1002/chem.202000525

  日期：2020.4.16

  hexanuclear trefoil knots featuring Cp*Rh building blocks by the template-free self-assembly of four different rigid and flexible ligands. Transformations between the trefoil knots and the corresponding macrocycles can be induced using concentration effects. Remarkably, the hexanuclear trefoil knot 5 was shown to assemble further, providing rare examples of [12+1] heteronuclear double trefoil knots ( 5a/5b/5c/5d

  理解和控制自组装结构的拓扑在超分子化学中起着基本作用。在这里，我们描述了通过四个不同的刚性和柔性配体的无模板自组装来制备一系列具有Cp * Rh构建基块的四核金属矩形和六核三叶结。三叶结与相应的大环之间的转化可以利用集中效应来诱导。值得注意的是，六核三叶结5进一步组装，通过酰胺氧原子与次要金属离子Na + / K +的配位提供了[12 + 1]异核双三叶结（5a / 5b / 5c / 5d）的罕见例子。 / Ca2 + / Cd2 +。合成结果得到单晶X射线衍射分析的支持。