N,N'-bis(2-pyrimidinyl)terephthalamide | 139522-10-4

• 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-pyrimidinyl)terephthalamide
• 英文别名: N,N'-bis(pyrimidin-2'-yl)benzene-1,4-dicarboxamide；N,N'-bis(2-pyrimidinyl)-1,4-benzenedicarboxamide；N,N'-dipyrimidin-2-ylterephthalamide；1-N,4-N-di(pyrimidin-2-yl)benzene-1,4-dicarboxamide
• CAS: 139522-10-4
• 化学式: C₁₆H₁₂N₆O₂
• mdl: MFCD01162856
• 分子量: 320.31
• InChiKey: TXRZUZQSSGAVKM-UHFFFAOYSA-N

物化性质

• 熔点：
  271 °C
• 密度：
  1.455±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  24
• 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：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  水 、 N,N'-bis(2-pyrimidinyl)terephthalamide 、 mercury dibromide 以 N,N-二甲基甲酰胺 为溶剂， 以26%的产率得到([HgBr2(N,N'-bis(2-pyrimidinyl)-1,4-benzenedicarboxamide)]*H2O)n
  参考文献：
  名称：

  Structural diversity in Cu(II), Cd(II) and Hg(II) coordination complexes with the rigid N,N′-bis(2/3-aryl)-1,4-benzenedicarboxamide ligand

  摘要：

  The syntheses and structures of a series of metal complexes, namely Cu2Cl4(L-1)(DMSO)(2)center dot 2DMSO (L-1 = N,N'-bis(2-pyridinyl)-1,4-benzenedicarboxamide), 1; {[Cu(L-2)(1.5)(DMF)(2)][ClO4](2)center dot 3DMF}(infinity) (L-2 = N,N'-bis(3pyridinyl)-1.4-benzenedicarboxamide), 2; {[Cd(NO3)(2)(L-3)]center dot 2DMF}(infinity) (L-3 = N,N'-bis-(2-pyrimidinyl)-1,4-benzenedicarboxamide), 3; {[HgBr2(L-3)]center dot H2O}(infinity), 4, and {[Na(L-3)(2)][Hg2X5]center dot 2DMF}(infinity) (X = Br, 5; 1, 6) are reported. All the complexes have been characterized by elemental analysis. IR spectra and single crystal X-ray diffraction. Complex 1 is dinuclear and the molecules are interlinked through S center dot center dot center dot S interactions. In 2, the Cu(II) ions are linked through the L-2 ligands to form 1-D ladder-like chains with 60-membered metallocycles, whereas complexes 3 and 4 form 1-D zigzag chains. In complexes 5 and 6, the Na(I) ions are linked by the L-3 ligands to form 2-D layer structures in which the [Hg2X5](-) anions are in the cavities. The L-2 ligand acts only as a bridging ligand, while L-1 and L-3 show both chelating and bridging bonding modes. The L-1 ligand in 1 adopts a trans-anti conformation and the L-2 ligand in 2 adopts both the cis-syn and trans-anti conformations, whereas the L-3 ligands in 3-6 adopt the trans conformation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2010.08.025
• 作为产物：
  描述：

  1,3,5-三嗪-2,4,6-三胺,N,N'''-1,2-乙二基二[N-[3-[[4,6-二[丁基(2,2,6,6-四甲基-4-哌啶基)氨基]-1,3,5-三嗪-2-基]氨基]丙基]-N,N''-二丁基-N,N''-二(2,2,6,6-四甲基-4-哌啶基)- 、 对苯二甲酰氯 在 N-甲基吡咯烷酮 、 lithium chloride 作用下， 反应 48.0h， 生成 N,N'-bis(2-pyrimidinyl)terephthalamide
  参考文献：
  名称：

  嘧啶二基刚性杆芳香聚酰胺的模型化合物的合成与X射线结构

  摘要：

  制备了各种基于嘧啶二基的刚性棒状聚酰胺聚[亚氨基-（嘧啶-2,5-二基）-亚氨基-四邻苯二甲酰基]（PPYMT）的模型化合物，以便将它们的构象与该化合物的几种模型化合物进行比较。相关的全芳族聚合物聚对苯二甲酰对苯二酰胺（PPTA）。特别地，通过X射线衍射测定了N-（2-嘧啶基）苯甲酰胺（PYMB）及其复合形式的双[（N-嘧啶-2-基）苯甲酰胺]二氯化镍（II）镍（IIPYMB）的结构。这些晶体中的分子堆积为我们提供了PPYMT纤维可能“交联”的模型。三聚体模型化合物N，N'-双（2-嘧啶基）对苯二甲酰胺（PYTA）和N的结构，N′-双（苯甲酰基）-2，5-二氨基嘧啶（BDAP）产生有关PPYMT链构象的信息，并与PPTA的类似模型化合物进行比较。

  DOI：

  10.1002/hlca.19920750116

文献信息

• Synthesis of<i>N</i>,<i>N</i>′‐<i>bis</i>(2‐Thiazolinyl)‐,<i>N</i>,<i>N</i>′‐<i>bis</i>(2‐Thiazolyl)‐, and<i>N</i>,<i>N</i>′‐<i>bis</i>(2‐Pyrimidinyl)‐Benzene Dicarboxamides
  作者：Sudershan R. Gondi、David Y. Son

  DOI：10.1081/scc-200028517

  日期：2004.1

  New heteroaromatic benzene dicarboxamides have been synthesized in moderate to good yields by the reactions of 2-aminothiazoline, 2-aminothiazole, and 2-aminopyrimidine with phthaloyl dichloride, isophthaloyl dichloride, and terephthaloyl dichloride in the presence of an organic base. The amides are sparingly soluble in common organic solvents but dissolve readily in dimethyl sulfoxide. Reactions of 2-aminothiazoline and 2-aminopyrimidine with phthaloyl dichloride yield a tricyclic compound and an imide, respectively, instead of the expected products.
• Syntheses and X-Ray Structures for Model Compounds of a Pyrimidinediyl-Based Rigid-Rod Aromatic Polyamide
  作者：Alfred G. Oertli、Werner R. Meyer、Ulrich W. Suter、Felix B. Joho、Volker Gramlich、Walter Petter

  DOI：10.1002/hlca.19920750116

  日期：1992.2.5

  A variety of model compounds for the pyrimidinediyl-based rigid-rod polyamide poly[imino-(pyrimidine-2,5-diyl)-imino-tetraphthaloyl] (PPYMT) was prepared, in order to compare their conformations to several model compounds of the related, fully aromatic polymer poly(p-phenyleneterephthalamide) (PPTA). In particular, the structures of N-(2-pyrimidyl)benzamide (PYMB) and its complexed form bis[(N-pyr

  制备了各种基于嘧啶二基的刚性棒状聚酰胺聚[亚氨基-（嘧啶-2,5-二基）-亚氨基-四邻苯二甲酰基]（PPYMT）的模型化合物，以便将它们的构象与该化合物的几种模型化合物进行比较。相关的全芳族聚合物聚对苯二甲酰对苯二酰胺（PPTA）。特别地，通过X射线衍射测定了N-（2-嘧啶基）苯甲酰胺（PYMB）及其复合形式的双[（N-嘧啶-2-基）苯甲酰胺]二氯化镍（II）镍（IIPYMB）的结构。这些晶体中的分子堆积为我们提供了PPYMT纤维可能“交联”的模型。三聚体模型化合物N，N'-双（2-嘧啶基）对苯二甲酰胺（PYTA）和N的结构，N′-双（苯甲酰基）-2，5-二氨基嘧啶（BDAP）产生有关PPYMT链构象的信息，并与PPTA的类似模型化合物进行比较。
• Structural diversity in Cu(II), Cd(II) and Hg(II) coordination complexes with the rigid N,N′-bis(2/3-aryl)-1,4-benzenedicarboxamide ligand
  作者：Ta-Pin Tsai、Yen-Tsang Huang、Umasankar Ray、Yin-Jui Chang、Pei-Chi Cheng、Chia-Jun Wu、Jhy-Der Chen、Ju-Chun Wang

  DOI：10.1016/j.poly.2010.08.025

  日期：2010.10

  The syntheses and structures of a series of metal complexes, namely Cu2Cl4(L-1)(DMSO)(2)center dot 2DMSO (L-1 = N,N'-bis(2-pyridinyl)-1,4-benzenedicarboxamide), 1; [Cu(L-2)(1.5)(DMF)(2)][ClO4](2)center dot 3DMF}(infinity) (L-2 = N,N'-bis(3pyridinyl)-1.4-benzenedicarboxamide), 2; [Cd(NO3)(2)(L-3)]center dot 2DMF}(infinity) (L-3 = N,N'-bis-(2-pyrimidinyl)-1,4-benzenedicarboxamide), 3; [HgBr2(L-3)]center dot H2O}(infinity), 4, and [Na(L-3)(2)][Hg2X5]center dot 2DMF}(infinity) (X = Br, 5; 1, 6) are reported. All the complexes have been characterized by elemental analysis. IR spectra and single crystal X-ray diffraction. Complex 1 is dinuclear and the molecules are interlinked through S center dot center dot center dot S interactions. In 2, the Cu(II) ions are linked through the L-2 ligands to form 1-D ladder-like chains with 60-membered metallocycles, whereas complexes 3 and 4 form 1-D zigzag chains. In complexes 5 and 6, the Na(I) ions are linked by the L-3 ligands to form 2-D layer structures in which the [Hg2X5](-) anions are in the cavities. The L-2 ligand acts only as a bridging ligand, while L-1 and L-3 show both chelating and bridging bonding modes. The L-1 ligand in 1 adopts a trans-anti conformation and the L-2 ligand in 2 adopts both the cis-syn and trans-anti conformations, whereas the L-3 ligands in 3-6 adopt the trans conformation. (C) 2010 Elsevier Ltd. All rights reserved.

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