2,6,2′,6′-tetranitro-biphenyl-4,4′-dicarboxylic acid | 84642-54-6

• 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: 2,6,2′,6′-tetranitro-biphenyl-4,4′-dicarboxylic acid
• 英文别名: 2,2',6,6'-tetranitro-4,4'-biphenyl dicarboxylic acid；2,2',6,6'-tetranitrobiphenyl-4,4'-dicarboxylic acid；4,4'-dicarboxy-2,2',6,6'-tetranitrobiphenyl；2,6,2',6'-tetranitro-biphenyl-4,4'-dicarboxylic acid；2,6,2',6'-Tetranitro-biphenyl-4,4'-dicarbonsaeure；4,4'-Dicarboxy-2,2',6,6'-tetranitro-biphenyl；4-(4-Carboxy-2,6-dinitrophenyl)-3,5-dinitrobenzoic acid
• CAS: 84642-54-6
• 化学式: C₁₄H₆N₄O₁₂
• 分子量: 422.221
• InChiKey: NDWWJIRHANYVLU-UHFFFAOYSA-N

物化性质

• 熔点：
  345-355 °C (decomp)
• 沸点：
  603.9±55.0 °C(Predicted)
• 密度：
  1.858±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  258
• 氢给体数：
  2
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,6,2′,6′-tetranitro-biphenyl-4,4′-dicarboxylic acid 在 sodium azide 、 硫酸 、 三氧化硫 作用下， 生成 4,4'-diamino-2,2',6,6'-tetranitrobiphenyl
  参考文献：
  名称：

  Nitrocarbons. 3. Synthesis of decanitrobiphenyl

  摘要：

  DOI：

  10.1021/jo00155a025
• 作为产物：
  描述：

  檀香(SANTALUMALBUM)提取物 在 硫酸 、 硝酸 作用下， 反应 48.0h， 生成 2,6,2′,6′-tetranitro-biphenyl-4,4′-dicarboxylic acid
  参考文献：
  名称：

  Thermal decomposition pathways of nitro-functionalized metal–organic frameworks

  摘要：

  通过脉冲反应传播的过程，硝化金属-有机框架转化为具有高度分散金属的碳结构。

  DOI：

  10.1039/c7cc03354k

文献信息

• Metal–Organic Frameworks Built from a Linear Rigid Dicarboxylate and Different Colinkers: Trap of the Keto Form of Ethylacetoacetate, Luminescence and Ferroelectric Studies
  作者：Tapan K. Pal、Rajesh Katoch、Ashish Garg、Parimal K. Bharadwaj

  DOI：10.1021/acs.cgd.5b00784

  日期：2015.9.2

  The ligand 2,6,2′,6′-tetranitro-biphenyl-4,4′-dicarboxylic acid (H2L) has been used alone or with a coligand to construct a number of metal organic frameworks (MOFs) with different metal ions that are X-ray crystallographically characterized. The porous three-dimensional (3D) MOF [Gd2(L)3(DMF)4]·(4DMF)·(3H2O)}n (1) (DMF = N,N′-dimethylformamide) is found to be an excellent host to the keto form of ethylacetoacetate to produce [Gd(L)1.5(DMF)2(H2O)2](S)(H2O)}n (1a) (S = ethyl 3-oxobutanoate) in single crystal to single crystal (SC–SC) transformation. This involves drastic rearrangement of the channels including several carboxylate shifts and concomitant movement of water molecules from the cavity to the metal center. Interestingly, the daughter framework 1a reverts back to the mother framework 1 upon keeping it in DMF for 3 days at room temperature, suggesting that the framework 1 can be used as a container. The linker H2L also forms the MOFs [(Cd)4(L)3(HlL1)2(DMF)(H2O)2](DMF)3(H2O)2}n (2), [Cd(L)(L2)]}n (3), [(Cd)1.5(L)1.5(L3)]}n (4), and [Cd(L)(L4)(H2O)]}n (5) in the presence of different colinkers. Solid-state photoluminescence studies performed on MOFs 2–5 at room temperature showed intraligand (π–π*) emission. The MOF 2 being a chiral compound has been subjected to ferroelectric measurements. All the compounds (1–5) have been characterized by X-ray crystallography, elemental analysis, powder X-ray diffraction patterns, thermogravimetry, and infrared spectroscopy.

  配体2,6,2′,6′-四硝基联苯-4,4′-二羧酸(H2L)单独使用或与共配体合用构筑了多种金属有机骨架(MOFs),其中不同的金属离子经X射线晶体学表征。多孔三维(3D)MOF [Gd2(L)3(DMF)4]·(4DMF)·(3H2O)}n(1)(DMF=N,N′-二甲基甲酰胺)被发现是乙酰乙酸乙酯的酮式结构的优秀的宿主,以单晶到单晶(SC–SC)转化的方式生成[Gd(L)1.5(DMF)2(H2O)2](S)(H2O)}n(1a)(S=乙基-3-氧代丁酸酯)。过程涉及包括若干羧酸盐位移及水分子从腔体到金属中心的伴随运动的通道重组。有趣的是,经过框架1a在室温下于DMF中放置3天,产物的母体框架1会还原回来,说明框架1能够用作容器。配体H2L也形成了MOF [(Cd)4(L)3(HlL1)2(DMF)(H2O)2](DMF)3(H2O)2}n(2)、[Cd(L)(L2)]}n(3)、[(Cd)1.5(L)1.5(L3)]}n(4)、[Cd(L)(L4)(H2O)]}n(5),这些都是在不同共配体存在下形成的。在室温下对MOFs 2~5进行了固体荧光性能的研究,发现有配体内(π–π*)发射。由于MOF 2是一种旋光化合物,所以对其进行了铁电性测定。所有的化合物(1~5)都经X射线晶体学、元素分析、粉末X射线衍射谱图、热重分析和红外光谱进行了表征。
• Assembly of Nickel(II) and Manganese(II) Coordination Polymers based on a Energetic Aromatic Dicarboxylic Acid Ligand
  作者：Rui-Feng Wu、Yong-Ji Zhu、Wei Jin

  DOI：10.1002/zaac.201300209

  日期：2013.10

  [Ni(tnbpdc)(H2O)4]·2H2O}n (1) and [Mn(tnbpdc)(H2O)4]·4H2O}n (2) (tnbpdc = 2, 2′,6, 6′-tetranitro-4, 4′-biphenyl dicarboxylic acid) were synthesized and structurally characterized by IR spectrocopy, elemental analysis, and X-ray diffraction. Complexes 1 and 2 adopt monodentate coordination modes and form two-dimensional layer structures by hydrogen bonds. The thermal results exhibit that both complexes

  配合物 [Ni(tnbpdc)(H2O)4]·2H2O}n (1) 和 [Mn(tnbpdc)(H2O)4]·4H2O}n (2) (tnbpdc = 2, 2′,6, 6 '-四硝基-4,​​ 4'-联苯二羧酸）被合成并通过红外光谱、元素分析和 X 射线衍射进行结构表征。配合物1和2采用单齿配位模式，通过氢键形成二维层状结构。热学结果表明，两种配合物都具有较高的热稳定性，但由于中心金属原子不同，分解温度也不同。它们可以用作新型的、结构相关的耐热含能材料。
• Synthesis and Characterization of a Metal-Organic Coordination Polymer
  作者：Rui-Feng Wu、Tong-Lai Zhang

  DOI：10.1002/zaac.201100462

  日期：2012.2

  A novel energetic microporous metal-organic coordination polymer [Ni(tnbpdc)(bpy)(H2O)2]·1.5(DMF)}n (1) (tnbpdc = 2, 2′,6, 6′-tetranitro-4, 4′-biphenyl dicarboxylate, bpy = 4, 4′-bipyridine) was prepared solvothermally and characterized by elemental, IR spectroscopic, and single-crystal X-ray diffraction analyses. The X-ray crystal structure of 1 revealed a rectangular-shaped grid constructed with

  一种新型含能微孔金属-有机配位聚合物[Ni(tnbpdc)(bpy)(H2O)2]·1.5(DMF)}n (1) (tnbpdc = 2, 2',6, 6'-tetranitro-4, 4'-联苯二羧酸酯 (bpy = 4, 4'-联吡啶) 以溶剂热法制备，并通过元素、红外光谱和单晶 X 射线衍射分析进行表征。1 的 X 射线晶体结构显示由 tnbpdc 接头和 bpy 接头构成的矩形网格，自由隧道尺寸估计为 11 × 15 A2。通过差示扫描量热法和热重分析评价该化合物的热稳定性。这种复合物可用作新型耐热含能材料。
• MOLECULAR DISSYMMETRY AND OPTICAL INACTIVITY
  作者：Kurt Mislow、Richard Bolstad

  DOI：10.1021/ja01629a131

  日期：1955.12
• Castle,R.N. et al., Journal of Heterocyclic Chemistry, 1969, vol. 6, p. 533 - 538
  作者：Castle,R.N. et al.

  DOI：——

  日期：——