3-amino-5-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)benzoic acid | 1208535-53-8

• 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-amino-5-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)benzoic acid
• 英文别名: 3-Amino-5-(3,5-dimethyl-1,2,4-triazol-4-yl)benzoic acid；3-amino-5-(3,5-dimethyl-1,2,4-triazol-4-yl)benzoic acid
• CAS: 1208535-53-8
• 化学式: C₁₁H₁₂N₄O₂
• 分子量: 232.242
• InChiKey: FSEUODIUYQHLIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  94
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-5-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)benzoic acid 以 水 、 乙腈 为溶剂， 反应 14.0h， 生成
  参考文献：
  名称：

  Network Flexibility: Control of Gate Opening in an Isostructural Series of Ag-MOFs by Linker Substitution

  摘要：

  An isostructural series of 15 structurally flexible microporous silver metal organic frameworks (MOFs) is presented. The compounds with a dinuclear silver core as secondary building unit (Ag2N4) can be obtained under solvothermal conditions from substituted triazolyl benzoate linkers and AgNO3 or Ag2SO4; they exhibit 2-fold network interpenetration with lvt topology. Besides the crystal structures, the calculated pore size distributions of the microporous MOFs are reported. Simultaneous thermal analyses confirm the stability of the compounds up to 250 degrees C. Interconnected pores result in a three-dimensional pore structure. Although the porosity of the novel coordination polymers is in the range of only 20-36%, this series can be regarded as a model system for investigation of network flexibility, since the pore diameters and volumes can be gradually adjusted by the substituents of the 3-(1,2,4-triazol-4-yl)-5-benzamidobenzoates. The pore volumes of selected materials are experimentally determined by nitrogen adsorption at 77 K and carbon dioxide adsorption at room temperature. On the basis of the flexible behavior of the linkers a reversible framework transformation of the 2-fold interpenetrated network is observed. The resulting adsorption isotherms with one or two hysteresis loops are interpreted by a gate-opening process. Due to external stimuli, namely, the adsorptive pressure, the materials undergo a phase transition confirming the structural flexibility of the porous coordination polymer.

  DOI：

  10.1021/ic500908r
• 作为产物：
  描述：

  2,5-二甲基-1,3,4-噁二唑 、 3,5-二氨基苯甲酸 在 对甲苯磺酸 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.0h， 以72%的产率得到3-amino-5-(3,5-dimethyl-4H-1,2,4-triazol-4-yl)benzoic acid
  参考文献：
  名称：

  高度官能化的3,4,5-三取代1,2,4-三唑可用作配位聚合物中的配体

  摘要：

  描述了可以用作金属有机骨架（MOF）接头的3,4,5-三取代的1,2,4-三唑的优化合成方法。三唑的3-和5-位上的取代基对芳环之间的扭转角具有显着影响，因此对这些配体的溶解性和配位行为具有影响。

  DOI：

  10.1016/j.tetlet.2009.11.098

文献信息

• ¹¹³Cd Solid-State NMR for Probing the Coordination Sphere in Metal-Organic Frameworks
  作者：Anusree Viswanath Kuttatheyil、Marcel Handke、Jens Bergmann、Daniel Lässig、Jörg Lincke、Jürgen Haase、Marko Bertmer、Harald Krautscheid

  DOI：10.1002/chem.201405395

  日期：2015.1.12

  material is unavailable. 113Cd solid‐state NMR is easy to measure and is a highly sensitive probe because the coordination number, the nature of coordinating groups, and the geometry around the metal ion is reflected by the isotropic chemical shift and the chemical‐shift anisotropy. Here, a detailed investigation of a series of 27 cadmium coordination polymers by 113Cd solid‐state NMR is reported. The results

  光谱技术是确定结构的强大工具，尤其是在没有单晶材料的情况下。113 Cd固态NMR易于测量并且是高度灵敏的探针，因为各向同性化学位移和化学位移各向异性反映了配位数，配位基团的性质以及金属离子周围的几何形状。在这里，通过113 Cd固态NMR对一系列27种镉配位聚合物进行了详细研究。获得的结果表明113Cd NMR是表征镉环境的非常敏感的工具，也适用于非单晶材料。此外，该方法还可以观察客体诱导的相变，从而有助于理解协调框架的结构灵活性。
• Highly functionalised 3,4,5-trisubstituted 1,2,4-triazoles for future use as ligands in coordination polymers
  作者：Daniel Lässig、Jörg Lincke、Harald Krautscheid

  DOI：10.1016/j.tetlet.2009.11.098

  日期：2010.1

  An optimised synthesis of 3,4,5-trisubstituted 1,2,4-triazoles, that can be used as linkers for metal organic frameworks (MOFs), is described. The substituents in 3- and 5-position of the triazole have a significant impact on the torsion angles between the aromatic rings and therefore influence on solubility and coordination behaviour of these ligands.

  描述了可以用作金属有机骨架（MOF）接头的3,4,5-三取代的1,2,4-三唑的优化合成方法。三唑的3-和5-位上的取代基对芳环之间的扭转角具有显着影响，因此对这些配体的溶解性和配位行为具有影响。
• Network Flexibility: Control of Gate Opening in an Isostructural Series of Ag-MOFs by Linker Substitution
  作者：Marcel Handke、Hanna Weber、Marcus Lange、Jens Möllmer、Jörg Lincke、Roger Gläser、Reiner Staudt、Harald Krautscheid

  DOI：10.1021/ic500908r

  日期：2014.7.21

  An isostructural series of 15 structurally flexible microporous silver metal organic frameworks (MOFs) is presented. The compounds with a dinuclear silver core as secondary building unit (Ag2N4) can be obtained under solvothermal conditions from substituted triazolyl benzoate linkers and AgNO3 or Ag2SO4; they exhibit 2-fold network interpenetration with lvt topology. Besides the crystal structures, the calculated pore size distributions of the microporous MOFs are reported. Simultaneous thermal analyses confirm the stability of the compounds up to 250 degrees C. Interconnected pores result in a three-dimensional pore structure. Although the porosity of the novel coordination polymers is in the range of only 20-36%, this series can be regarded as a model system for investigation of network flexibility, since the pore diameters and volumes can be gradually adjusted by the substituents of the 3-(1,2,4-triazol-4-yl)-5-benzamidobenzoates. The pore volumes of selected materials are experimentally determined by nitrogen adsorption at 77 K and carbon dioxide adsorption at room temperature. On the basis of the flexible behavior of the linkers a reversible framework transformation of the 2-fold interpenetrated network is observed. The resulting adsorption isotherms with one or two hysteresis loops are interpreted by a gate-opening process. Due to external stimuli, namely, the adsorptive pressure, the materials undergo a phase transition confirming the structural flexibility of the porous coordination polymer.