N,N'-bis(pyridin-4-ylmethyl)oxalamide | 205386-51-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N'-bis(pyridin-4-ylmethyl)oxalamide
• 英文别名: N,N'-bis-pyridin-4-ylmethyl-oxalamide；N,N-bis(pyridin-4-ylmethyl)oxalamide；N,N'-bis(4-methylpyridyl)oxalamide；N,N'-bis(4-pyridylmethyl)oxalamide；N,N'-bis-4-methylpyridyl oxalamide；4-pyridyl-CH2NHCOCONHCH2-4-pyridyl；Ethanediamide, N,N'-bis(4-pyridinylmethyl)-；N,N'-bis(pyridin-4-ylmethyl)oxamide
• CAS: 205386-51-2
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: IMFIKLLSTFRMNN-UHFFFAOYSA-N

物化性质

• 密度：
  1.261±0.06 g/cm3(Predicted)
• 溶解度：
  >40.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 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'-bis(pyridin-4-ylmethyl)oxalamide 在 劳森试剂 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 以100%的产率得到N,N'-bis(pyridin-4-ylmethyl)thioxalamide
  参考文献：
  名称：

  A New Convergent Synthesis of 4,4′-Bispyridyl-5,5′-Disubstituted-2,2-Bisoxazoles and -Bisthiazoles

  摘要：

  实现了从二酰胺合成 4,4′-二吡啶基-5,5′-二取代-2,2′-双噁唑和双噻唑的聚合策略。

  DOI：

  10.1055/s-2003-42085
• 作为产物：
  描述：

  4-甲氨基吡啶 、 草酸二乙酯 反应 0.33h， 以84%的产率得到N,N'-bis(pyridin-4-ylmethyl)oxalamide
  参考文献：
  名称：

  Single-Crystal-to-Single-Crystal Topochemical Polymerizations of a Terminal Diacetylene:  Two Remarkable Transformations Give the Same Conjugated Polymer

  摘要：

  Host-guest chemistry was used to prepare a cocrystal of a dipyridyl substituted oxalamide host and a resorcinol derivative of a terminal diacetylene. X-ray crystallography revealed that the molecules assemble into a triple-helix with the diacetylene functionalities aligned in the center of the helix. Upon heating, the diacetylenes polymerize to give the corresponding polymer. In a second experiment, the X-ray structure of the crystalline hydrate of the same diacetylene also showed a suitable alignment of the diacetylene functionalities. These crystals polymerize at only 50 degrees C with the C1 carbon end of the diacetylene undergoing an unprecedented 2.4 A inward swinging movement. This results in a remarkable 9% increase in crystal density. These are the first structurally characterized polymerizations of any terminal diacetylene. A detailed comparison of the two sets of structural changes offers an interesting insight into the precise trajectories of polymerization reactions.

  DOI：

  10.1021/ja037557+

文献信息

• Directing the Crystallization of Dehydro[24]annulenes into Supramolecular Nanotubular Scaffolds
  作者：Mitsuharu Suzuki、Juliet F. Khosrowabadi Kotyk、Saeed I. Khan、Yves Rubin

  DOI：10.1021/jacs.6b01939

  日期：2016.5.11

  We have studied the parameters affecting self-assembly, including the nature of the substituent and crystallization conditions, using 10 different dehydro[24]annulene derivatives. In particular, hydrogen-bonding interactions through carbamate groups were found to be especially useful at directing the formation of nanotubular supramolecular assemblies. We have also evaluated the electronic coupling

  已经研究了一系列脱氢 [24] 环烯衍生物自组装成柱状堆叠的潜在能力，通过拓扑化学聚合形成 π 共轭富碳纳米管结构。我们使用 10 种不同的脱氢 [24] 环烯衍生物研究了影响自组装的参数，包括取代基的性质和结晶条件。特别是，发现通过氨基甲酸酯基团的氢键相互作用在指导纳米管超分子组装体的形成方面特别有用。我们还评估了这些超分子组件内相邻脱氢环烯分子之间的电子耦合。堆叠超分子纳米管组件的密度泛函计算表明，三个柱状组件之间的转移积分差异很大，从中等到高（最高占据分子轨道为 59-98 meV，最低未占据分子轨道为 63-97 meV），取决于局部分子拓扑。此外，脱氢[24]环烯衍生物在晶体中提供了独特的结构，包括纳米通道阵列、带有溶剂填充孔的薄片和薄片。这项工作是朝着受控形成共价连接的富碳纳米结构迈出的重要一步，该结构由具有潜在丁二炔反应性的分子前体产生。最低未占分子轨道为 63-97 meV
• Preparation, characterization and luminescence-sensing properties of two Zn^II MOFs with mixed 5-amino-2,4,6-tribromoisophthalic acid and bipyridyl-type ligands
  作者：Jie Xu、Kou-Lin Zhang

  DOI：10.1107/s2053229619007435

  日期：2019.7.1

  topological network. The supramolecular interactions (π–π stacking, hydrogen bonding and C—Br…Br halogen bonding) play significant roles in the formation of an extended three‐dimensional (3D) supramolecular network of (1). Complex (2) crystallizes in the chiral space group P212121 and exhibits a novel 3D homochiral framework, showing a diamond‐like topology with Schläfli symbol 66. The homochirality of (2)

  在N-给体柔性双吡啶基型配体1,3-双（吡啶-4-基）存在的情况下，溴取代的芳族二羧酸5-氨基-2,4,6-三溴间苯二甲酸（H 2 ATBIP）丙烷（bpp）和N，N'-双（吡啶-4-基甲基）草酰胺（4-bpme）和Zn II离子被用作O-供体配体，组装了两个新颖的发光金属-有机骨架（MOF），即聚[[（μ-5-氨基-2,4,6- tribromoisophthalato-κ 2 ø 1：ö 3）[μ-1,3-二（吡啶-4-基）丙烷κ 2 ñ：ñ ' ]锌（II）]二甲基甲酰胺单溶剂化物]，[Zn（C 8 H 2 Br 3NO 4）（C 13 H ^ 14 Ñ 2）]·C 3 H ^ 7 NO} Ñ，（1），和聚[[（μ-5-氨基-2,4,6- tribromoisophthalato-κ 2 ø 1：Ò 3）二水[μ- ñ，ñ ' -双（吡啶-4-基甲基）草酰胺-κ 2 ñ：ñ ']锌（II）]一水合物]，[锌（C
• Crystal-Engineering Studies of Coordination Polymers and a Molecular-Looped Complex Containing Dipyridyl-Amide Ligands
  作者：Biing-Chiau Tzeng、Yung-Chi Huang、Bo-So Chen、Wan-Min Wu、Shih-Yang Lee、Gene-Hsiang Lee、Shie-Ming Peng

  DOI：10.1021/ic061528t

  日期：2007.1.1

  structural backbone from L1 to L2, the reaction of L2 with Cd(OAc)2 gives [Cd(OAc)2(L2)(H2O)]n (2), a 1-D chain structure. The reaction of Cd(NO3)2, instead of Cd(OAc)2, with L2 gives [Cd(NO3)2(L2)3/2]n (3), where the coordinated-anion effect on the assembly process has been observed for 2 and 3. The former forms a 1-D chain structure, and the latter, a 2-D sheet structure, depending on the coordinated

  我们在这里报告配位聚合物和包含两个双吡啶基酰胺配体，1,3-双吡啶-4-基甲基尿素（L1）和N，N'-双-4-甲基吡啶基草酰胺的分子环复合物的晶体工程研究（L2）。Cd（OAc）2与L1的反应生成[Cd（OAc）2（L1）] n（1），通过与两个L1和两个乙酸酯配体的配位形成一维链，然后与一个L1轴向配位尿素的羰基通过第三个L1配体导致1形成“ 1-D链的二聚体”。在从L1到L2的结构主链上发生微小变化的情况下，L2与Cd（OAc）2的反应得到[Cd（OAc）2（L2）（H2O）] n（2），一维链结构。Cd（NO3）2代替Cd（OAc）2与L2的反应生成[Cd（NO3）2（L2）3/2] n（3），其中对组装过程的配位阴离子效应为观察2和3。前者形成一维链状结构，后者形成二维片状结构，具体取决于所用的配位阴离子。作为一维链结构的[HgCl2（L1）] n（4）和[CuCl2（L2）] n
• Supramolecular Assembly of Gold(I) Complexes of Diphosphines and <i>N</i>,<i>N</i><i>‘</i>-Bis-4-methylpyridyl Oxalamide
  作者：Biing-Chiau Tzeng、Hsien-Te Yeh、Ya-Ling Wu、Jau-Huei Kuo、Gene-Hsiang Lee、Shie-Ming Peng

  DOI：10.1021/ic051297a

  日期：2006.1.1

  the supramolecular assembly and spectroscopic and luminescent properties of gold(I) complexes of diphosphines (dppm [bis(diphenylphosphino)methane], dppp [1,3-bis(diphenylphosphino)propane], and dpppn [1,5-bis(diphenylphosphino)pentane]) and N,N'-bis-4-methylpyridyl oxalamide (L). The dppm and dppp cases form the rectangular structures, [dppm(Au(2))L](2)(ClO(4))(4) and [dppp(Au(2))L](2)(ClO(4))(4)

  我们在此报告了双膦类化合物（dppm [双（二苯基膦基）甲烷]，dppp [1,3-双（二苯基膦基）丙烷]和dpppn [1,5-bis]的金（I）配合物的超分子组装以及光谱和发光特性（二苯基膦基）戊烷]）和N，N'-双-4-甲基吡啶基草酰胺（L）。dppm和dppp情况形成矩形结构[dppm（Au（2））L]（2）（ClO（4））（4）和[dppp（Au（2））L]（2）（ClO（4） ））（4），在拐角处有四个金（I）离子，以及两个L和两个dppm或dppp配体作为边缘，前者和后者分别具有38和42元环。值得注意的是，dppp配合物的堆积显示出有趣的固态一维矩形通道，这很可能是由于分子间pi ... pi相互作用所致。dpppn配合物在结构上已表征为一维配位聚合物，[（dpppn）（3.5）（Au（7））L（3.5）]（PF（6））（7）}。化合物的吸收和发射通常归因于配体内部的过渡，但亲酸或pi
• Pressure induced topochemical polymerization of diiodobutadiyne: a single-crystal-to-single-crystal transformation
  作者：Hongjian Jin、Anna M. Plonka、John B. Parise、Nancy S. Goroff

  DOI：10.1039/c3ce26851a

  日期：——

  Diiodobutadiyne forms cocrystals with bis(pyridyl)oxalamides, based on halogen bonds between the pyridine groups of the host and the iodoalkynes of the guest. These interactions align the diyne for topochemical polymerization to form poly(diiododiacetylene) or PIDA. To induce polymerization, the crystals are subjected to pressures of 3.5 GPa or above. Previously, we reported spectroscopic evidence of this pressure-induced polymerization, but attempts to recover single crystals after pressure treatment were unsuccessful. Here we present direct structural evidence of clean single-crystal to single-crystal polymerization in these cocrystals. The structure of the polymer cocrystal was solved from single-crystal diffraction data and is supported by high pressure in situ Raman spectroscopy. Careful analysis of the structural changes suggests that increasing pressure changes the packing of host molecules, and that the flexibility of the pyridine ring orientation enables the polymerization. The new sigma bonds of the polymer form at the expense of the halogen bonds in the starting cocrystal; after polymerization, the iodine atoms are no longer ideally located for strong halogen bonding with the host.

  基于主体的吡啶基团和客体的碘代炔之间的卤素键，二碘丁二炔与双(吡啶基)草酰胺形成共晶。这些相互作用使二炔排列进行拓扑化学聚合，形成聚（二碘二乙炔）或PIDA。为了引发聚合，晶体需要承受 3.5 GPa 或更高的压力。此前，我们报道了这种压力诱导聚合的光谱证据，但在压力处理后恢复单晶的尝试并未成功。在这里，我们提出了这些共晶中干净的单晶到单晶聚合的直接结构证据。聚合物共晶的结构是根据单晶衍射数据解析出来的，并得到高压原位拉曼光谱的支持。对结构变化的仔细分析表明，增加压力会改变主体分子的堆积，并且吡啶环方向的灵活性能够实现聚合。聚合物的新西格玛键的形成是以起始共晶中的卤素键为代价的；聚合后，碘原子不再处于与主体形成强卤素键合的理想位置。