3,4-pyrazoledicarboxylic acid | 35344-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,4-pyrazoledicarboxylic acid
• 英文别名: 3,4-Pyrazol-dicarbonsaeure；1H-pyrazole-3,4-dicarboxylic acid；1H-pyrazole-4,5-dicarboxylic acid
• CAS: 35344-99-1
• 化学式: C₅H₄N₂O₄
• mdl: MFCD00229565
• 分子量: 156.098
• InChiKey: IKTPUTARUKSCDG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-pyrazoledicarboxylic acid 生成 吡唑
  参考文献：
  名称：

  v. Pechmann; Seel, Chemische Berichte, 1899, vol. 32, p. 2297

  摘要：

  DOI：
• 作为产物：
  描述：

  diethyl(ethoxymethylene)oxalacetate 在 肼 作用下， 反应 2.0h， 生成 3,4-pyrazoledicarboxylic acid
  参考文献：
  名称：

  vic-DICARBOXYLIC ACID DERIVATIVES OF PYRAZOLE, ISOXAZOLE, AND PYRIMIDINE

  摘要：

  DOI：

  10.1021/jo01127a008

文献信息

• Studies directed toward the prediction of the oxidative reactivity of vanadium peroxo complexes in water. Correlations between the nature of the ligands and 51V-NMR chemical shifts
  作者：Valeria Conte、Fulvio Di Furia、Stefano Moro

  DOI：10.1016/1381-1169(95)00143-3

  日期：1995.12

  ability of the ligands and the energy gap HOMO-LUMO of the peroxo complexes are linearly correlated. All these observations indicate that peroxo vanadium complexes containing strongly electron donating ligands should be weak electrophilic oxidants and poor one-electron acceptors. Preliminary data concerning the reactivity of a series of peroxo vanadium species in the simple self-decomposition reaction confirm

  研究了一系列钒过氧配合物在水中的51 V-NMR光谱行为。考察了含有两个结合位点是氧原子（O = O配体）或一个氧和一个氮原子（N = O配体）的二齿配体的单过氧钒配合物，以及含有各种取代的吡啶或苯胺的二氧杂钒配合物。在所有情况下，均观察到金属的磁屏蔽与配体的电子特性直接相关，该金属屏蔽通过其51 V-NMR化学位移测量。对于双二恶英配合物之间的Hammett型相关性为51建立了V-NMR化学位移和吡啶或苯胺环中取代基的σ值。对于一元过氧化物配合物，发现了化学位移与配体-金属电荷转移电子跃迁的能量之间的拉姆齐型相关性，从而表明该配体的给电子能力和过氧配合物的能隙HOMO-LUMO是线性相关的。所有这些观察结果表明，含有强给电子配体的过氧钒络合物应为弱亲电子氧化剂和较弱的单电子受体。关于一系列过氧钒物种在简单的自分解反应中的反应性的初步数据证实了这一预测。
• Highly efficient Cu(<scp>ii</scp>)-pyrazoledicarboxylate heterogeneous catalysts for a base-free aerobic oxidation of benzylic alcohol to benzaldehyde with hydrogen peroxide as the oxidant
  作者：Mei-Ling Cheng、Meng-Na Qin、Lin Sun、Lu Liu、Qi Liu、Xiao-Yan Tang

  DOI：10.1039/c9dt04927d

  日期：——

  a μ3-κO: κN, O′: κN′ mode, forming a two-dimensional (2D) (4,4) network; the other ImH ligand acted as a terminal ligand. Cu(II)-MOF 1 displayed high activity and selectivity in the base-free aerobic oxidation of benzyl alcohol to benzaldehyde combined with the green oxidant H2O2. The catalytic system of 1 could be reused for several cycles without any obvious decay of the catalytic efficiency.

  一种新型的Cu（II）吡唑二羧酸配位聚合物[Cu（Hpdc）（ImH）] n（1）（H 3 pdc = 3,4-吡唑二羧酸; ImH =咪唑）已水热合成并通过元素分析，FT-红外，X射线衍射和热重分析。在1，四齿HPDC 2-阴离子配位至三个的Cu（II）离子在μ 3 -κO：κN，O'：κN'模式，形成一个二维（2D）（4,4）网络; 另一个ImH配体充当末端配体。铜（II）-MOF 1苯甲醇与绿色氧化剂H 2 O 2结合，在无碱好氧氧化苄醇生成苯甲醛中显示出高活性和选择性。的催化系统1可以被重新用于几个循环而没有的催化效率任何明显的腐烂。
• Metal-to-Ligand Ratio Controlled Assembly of Two Ni(II) Complexes: Structures, Luminescent and Electrochemical Properties
  作者：Mei-Ling Cheng、Lu Liu、Lin Sun、Feng Tao、Meng-Na Qin、Qi Liu、Xiao-Yan Tang

  DOI：10.1007/s10870-020-00854-1

  日期：2021.6

  Treatment of Ni(OAc)2·4 H2O with 3,4-pyrazoledicarboxylic acid (H3pdc) and imidazole (ImH) in different metal-to-ligand ratios afforded two dinuclear nickel(II) complexes, [Ni(Hpdc)(ImH)(H2O)2]2·4 H2O (1) and [Ni(Hpdc)(ImH)2(H2O)]2·2.5 H2O (2), which were characterized by elemental analysis (EA), IR spectra and X-ray diffraction analysis and thermogravimetric analysis (TGA). Both in 1 and 2, the dinickle unit [Ni2(µ2-Hdpc)2] with six-numbered Ni2N4 ring was formed by a pair of µ2-Hpdc2− ligands linked two Ni(II) ions in N,O-chelating and N‒N-bridging fashions. The dinuclear units in 1 and 2 were expanded to 2D layer structures though hydrogen-bonding interactions between coordination water molecules, ImH molecules and carboxylate oxygen atoms, whereas the lattice water molecules in 1 and 2 just embedded in the 2D layer through intermolecular hydrogen bonding interactions. Finally, the 2D sheets in 1 were further assembled to a 3D supramolecular architecture via intermolecular C–H⋯O hydrogen bond. Besides, the luminescent and electrochemical properties of two complexes have been reported. Two dinuclear nickel(II) complexes, [Ni(Hpdc)(ImH)(H2O)2]2·4 H2O (1) and [Ni(Hpdc)(ImH)2(H2O)]2·2.5 H2O (2), were obtained by assembling of a Ni(II) ion, 3,4-pyrazoledicarboxylic acid (H3pdc) and imidazole (ImH) in different metal-to-ligand ratios. In 1 and 2, the O(C, N)−H⋯O hydrogen bonds expanded the dinuclear complexes to 3D/2D supramolecular structures, respectively.

  2中，由一对µ2-Hpdc2−配体以N,O螯合和N‒N桥联的方式连接两个Ni(II)离子，形成具有六元Ni2N4环的双镍单元[Ni2(µ2-Hdpc)2]。1和2中的双核单元通过配位水分子、ImH分子和羧酸氧原子之间的氢键相互作用扩展为二维
• Two Metal Complexes Based on the Ligand 3, 4-Pyrazoledi­carboxylic Acid: Synthesis, Structures, and Luminescent ­Properties
  作者：Linti Chen、Feng Tao、Lidong Wang、Jian Hong、Xiaoyan Jia、Jinting Bao、Yunzhou Ji、Meiling Cheng、Qi Liu

  DOI：10.1002/zaac.201200486

  日期：2013.3

  Two new metal complexes, [Cd2(μ2-H2pdc)2(H2O)8]·[Cd2(H2pdc)4(H2O)2(μ2-Cl)2]}·2H2O (1), and [Ba2(H2pdc)4(H2O)8]·2H2O (2) (H3pdc = 3, 4-pyrazoledicarboxylic acid), were synthesized and characterized by elemental analysis, IR spectroscopy, and single-crystal X-ray diffraction. The crystal structures show that compound 1 is an independent unit consisting of two discrete dinuclear complex ions [Cd2(μ2-H2pdc)2(H2O)8]2+

  两种新的金属配合物，[Cd2(μ2-H2pdc)2(H2O)8]·[Cd2(H2pdc)4(H2O)2(μ2-Cl)2]}·2H2O(1)和[Ba2(H2pdc) 4(H2O)8]·2H2O (2) (H3pdc = 3, 4-吡唑二甲酸) 被合成并通过元素分析、红外光谱和单晶X 射线衍射表征。晶体结构表明，化合物1是一个独立的单元，由两个离散的双核络离子[Cd2(μ2-H2pdc)2(H2O)8]2+阳离子和[Cd2(H2pdc)4(H2O)2(μ2-Cl) 2]2– 阴离子，两种离子通过氢键和静电相互作用连接，形成3D超分子网络。配合物 2 是一种常见的双核结构，通过分子间氢键和 π-π 堆栈进一步组装成 3D 超分子网络。涉及晶格水或配位水分子的氢键相互作用均存在于配合物 1 和 2 中。值得注意的是，观察到 3, 4-吡唑二甲酸的三种配位模式。还研究了固态配合物 1 和 2 的热和光致发光特性。
• Tyupalo, N. F.; Semenyuk, T. N.; Kolbasina, O. I., Russian Journal of Physical Chemistry, 1992, vol. 66, # 4, p. 463 - 465
  作者：Tyupalo, N. F.、Semenyuk, T. N.、Kolbasina, O. I.

  DOI：——

  日期：——