2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid
• 英文别名: 2-(3-Carboxylphenyl)-1h-imidazole-4,5-dicarboxylic acid；2-(3-carboxyphenyl)-1H-imidazole-4,5-dicarboxylic acid
• 化学式: C₁₂H₈N₂O₆
• 分子量: 276.205
• InChiKey: HDOZQJWRHMGQFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.0
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid 、 aqueous cadmium chloride 在 三乙胺 作用下， 以 乙醚 、 水 为溶剂， 反应 72.0h， 以63%的产率得到{[Cd3(2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid(-3H))2(H2O)8]·2H2O}n
  参考文献：
  名称：

  Construction of a series of coordination polymers from three imidazole-based multi-carboxylate ligands

  摘要：

  在咪唑-4,5-二甲酸酯体系的 2 位分别引入 2-羧基苯基、3-羧基苯基和 4-羧基苯基，得到三种多功能配体 2-(2-羧基苯基)-1H-咪唑-4、5-二羧酸（o-CPH4IDC）、2-（3-羧基苯基）-1H-咪唑-4,5-二羧酸（m-CPH4IDC）和 2-（4-羧基苯基）-1H-咪唑-4,5-二羧酸（p-CPH4IDC）。然后，这三种有机配体与 Sr(II) 和 Cd(II) 离子发生反应。随后，[Sr(o-CPh2IDC)]n (1)、[Sr3(m-CPh2IDC)2(H2O)3]n (2)、[Sr(p-CPh2IDC)(H2O)]n (3) 五种三维或二维聚合物被制成、[n (4)和{[Cd3(m-CPhH2IDC)2(H2O)8]-2H2O}n (5)进行了水（溶）热合成和结构表征。化合物 1 是一种 (5,5) 连接的三维结构，具有独特的 "H 形 "通道。在化合物 2 中，Sr 原子周围呈现出三种配位环境。化合物 1 和 2 都含有不寻常的不规则笼。化合物 3 显示了一个 (4,6) 连接的三维多孔框架，由对-CPH2IDC2-阴离子连接的右手螺旋组成。化合物 4 和 5 都呈现出网状层结构。这些不同的结构展示了这三种咪唑基多羧酸配体的多功能配位能力。

  DOI：

  10.1039/c3dt51486b

文献信息

• Imidazole Multi-Carboxylate-Based 2D Cd(II) MOF: Preparation, Crystal Structure, and Properties
  作者：Y. Zhao、D. D. Zhao、H. L. Liu、W. Y. Zhou、G. Li

  DOI：10.1134/s1070328420040089

  日期：2020.4

  4H2O}n (I) has been sucessfully constructed. The structure has been determined by single-crystal X-ray diffraction analysis (CIF files CCDC no. 1480230) and further characterized by elemental analyses, IR spectra, and thermogravimetric analysis. MOF I exhibits a rare (3,4)-connected 2D structure bearing two kinds of organic ligands. According to the crystal data, the coordination ability and mode of the

  摘要通过采用一个咪唑多羧酸盐配体，2-（3-羧基苯基）-1 H-咪唑-4,5-二羧酸（m -CPhH 4 IDC）和一个含氮配体2,2'-联吡啶（2 ，2'-Bipy）在溶剂热条件下与二维金属有机骨架[Cd 6（m -CPhHIDC）4（2,2'-Bipy）6 ]·与Cd（NO 3）2反应。 4H 2 O} n（I）已成功构建。该结构已通过单晶X射线衍射分析（CIF文件CCDC 1480230）确定，并进一步通过元素分析，IR光谱和热重分析进行了表征。MOF I展示了一种稀有的（3,4）连接的2D结构，带有两种有机配体。根据晶体数据，讨论了咪唑多羧酸盐配体的配位能力和方式。此外，已经研究了MOF I的热稳定性和固态光致发光性质。
• Three metal–organic frameworks constructed from imidazole-based multi-carboxylate ligands: Syntheses, structures and photoluminescent properties
  作者：Wenyan Zhou、Lijia Zhao、Zilong An、Gang Li

  DOI：10.1016/j.poly.2016.05.059

  日期：2016.10

  Abstract Three metal–organic frameworks, [Ba(o-CPhH2IDC)]n (1), [Ca(o-CPhH2IDC)(H2O)2]·H2O}n (2), (o-CPhH4IDC = 2-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid) and [Cd(m-CPhH2IDC)(phen)]·H2O}n (3) (m-CPhH4IDC = 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid and phen = 1,10-phenanthroline), have been solvothermally synthesized and structurally characterized by elemental analyses

  摘要三种金属有机骨架，[Ba（o-CPhH2IDC）] n（1），[Ca（o-CPhH2IDC）（H2O）2]·H2O} n（2），（o-CPhH4IDC = 2-（2 -羧基苯基）-1H-咪唑-4,5-二羧酸）和[Cd（m-CPhH2IDC）（phen）]·H2O} n（3）（m-CPhH4IDC = 2-（3-羧基苯基）-1H-溶剂热合成咪唑（4,5-二羧酸和phen = 1,10-菲咯啉），并通过元素分析，红外光谱，热重分析和单晶X射线衍射对其结构进行了表征。化合物1是（5,5）连接的3D结构。化合物2显示无限的一维双链结构。复数3通过相邻之字形链的π–π相互作用呈现出一种波状结构。咪唑基多羧酸盐配体具有很强的配位能力和多种配位方式。此外，
• Two Manganese(II) Supramolecular Complexes Based on Imidazole Dicarboxylates: Syntheses, Crystal Structures, and Properties
  作者：Jie Li、Beibei Guo、Shaofeng Liu、Gang Li

  DOI：10.1080/15533174.2013.797463

  日期：2014.8.9

  Two novel Mn(II) complexes [Mn(MDPhH2IDC)2(H2O)2] n (1) (MDPhH3IDC = 2-(3,4-methylenedioxyphenyl)-1H-imidazole-4, 5-dicarboxylic acid), [Mn( m-CPhH3IDC)2(H2O)2] n (2) (m-CPh H4IDC = 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid) have been hydrothermally synthesized with two kinds of imidazole dicarboxylate ligands, respectively, and structurally characterized by elemental analyses, IR spectra

  两个新的Mn（II）配合物[Mn（上MDPhH 2 IDC）2（H 2 O）2 ] Ñ（1）（MDPhH 3 IDC = 2-（3,4-亚甲二氧苯基）- 1 H ^ -咪唑-4-，5-二羧酸），[Mn （m -CPhH 3 IDC）2（H 2 O）2 ] n（2）（m -CPh H 4 IDC = 2-（3-羧基苯基）-1 H -咪唑-4,5-二羧酸）分别由两种咪唑二羧酸酯配体进行水热合成，并通过元素分析，红外光谱和单晶X射线衍射分析对其结构进行了表征。配合物的3D固态超分子结构涉及分子间氢键。此外，已经研究了配合物的热和光致发光性质。
• Syntheses, structures and thermal properties of four manganese coordination polymers from imidazole-based multi-carboxylates
  作者：Guoqing Shi、Bingbing Shi、Qi Wang、Gang Li

  DOI：10.1016/j.poly.2015.03.026

  日期：2015.5

  By using two types of carboxylphenyl-based imidazole-4,5-dicarboxylic acids, four coordination polymers, [Mn(o-CPhH2IDC)(H2O)(2)](n) (1), [Mn-3(m-CPhHIDC)(2)(phen)(2)](n) (2) (m-CPhH4IDC = 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid), [Mn-3(o-CPhHIDC)(2)(phen)(3)]center dot H2O}(n) (phen = 1,10-phenanthroline) (3) and [Mn-3(o-CPhHIDC)(2)(2,2'-bipy)(3)]center dot(2,2'-bipy)(0.5))}(n) (2,2'-bipy = 2,2'-bipyridine) (4), have been synthesized and characterized by elemental analyses, IR, thermogravimetric analyses and single-crystal X-ray diffraction. Compound 1 crystallizes as a 2-D four-connected 4(4)-sql network. Polymer 2 has a 3-D architecture with a net point group of 4(3).8(7)}4(3)}4(6).8(4)}(2). Complexes 3 and 4 present wave-like architectures by pi-pi interactions from neighboring zigzag chains. These various architectures demonstrate the versatile coordination abilities of the imidazole-based multi-carboxylate ligand. The thermal properties of the complexes have also been investigated. (C) 2015 Elsevier Ltd. All rights reserved.
• Construction of a series of coordination polymers from three imidazole-based multi-carboxylate ligands
  作者：Beibei Guo、Li Li、Yang Wang、Yanyan Zhu、Gang Li

  DOI：10.1039/c3dt51486b

  日期：——

  2-Carboxylphenyl, 3-carboxylphenyl and 4-carboxylphenyl groups were introduced into the 2-position of imidazole-4,5-dicarboxylate system, respectively, obtaining three multi-functional ligands 2-(2-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid (o-CPhH4IDC), 2-(3-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid (m-CPhH4IDC) and 2-(4-carboxylphenyl)-1H-imidazole-4,5-dicarboxylic acid (p-CPhH4IDC). Then the three organic ligands are employed to react with Sr(II) and Cd(II) ions. Subsequently, five 3D or 2D polymers, [Sr(o-CPhH2IDC)]n (1), [Sr3(m-CPhHIDC)2(H2O)3]n (2), [Sr(p-CPhH2IDC)(H2O)]n (3), [Cd(o-CPhH2IDC)(H2O)2]n (4) and [Cd3(m-CPhHIDC)2(H2O)8]·2H2O}n (5), have been hydro(solvo)thermally synthesized and structurally characterized. Compound 1 is a (5,5)-connected 3D structure with unique “H-shape” channels. Three kinds of coordination environments around the Sr atoms are exhibited in compound 2. Both compounds 1 and 2 contain unusual irregular cages. Compound 3 displays a (4,6)-connected 3D porous framework composed of right-handed helices connected by p-CPhH2IDC2− anions. Both compounds 4 and 5 present net-like layer structures. These various architectures demonstrate the versatile coordination abilities of the three imidazole-based multi-carboxylate ligands.

  在咪唑-4,5-二甲酸酯体系的 2 位分别引入 2-羧基苯基、3-羧基苯基和 4-羧基苯基，得到三种多功能配体 2-(2-羧基苯基)-1H-咪唑-4、5-二羧酸（o-CPH4IDC）、2-（3-羧基苯基）-1H-咪唑-4,5-二羧酸（m-CPH4IDC）和 2-（4-羧基苯基）-1H-咪唑-4,5-二羧酸（p-CPH4IDC）。然后，这三种有机配体与 Sr(II) 和 Cd(II) 离子发生反应。随后，[Sr(o-CPh2IDC)]n (1)、[Sr3(m-CPh2IDC)2(H2O)3]n (2)、[Sr(p-CPh2IDC)(H2O)]n (3) 五种三维或二维聚合物被制成、[n (4)和[Cd3(m-CPhH2IDC)2(H2O)8]-2H2O}n (5)进行了水（溶）热合成和结构表征。化合物 1 是一种 (5,5) 连接的三维结构，具有独特的 "H 形 "通道。在化合物 2 中，Sr 原子周围呈现出三种配位环境。化合物 1 和 2 都含有不寻常的不规则笼。化合物 3 显示了一个 (4,6) 连接的三维多孔框架，由对-CPH2IDC2-阴离子连接的右手螺旋组成。化合物 4 和 5 都呈现出网状层结构。这些不同的结构展示了这三种咪唑基多羧酸配体的多功能配位能力。