4,4'-dichloro-3,3'-azobenzenedicarboxylic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 4,4'-dichloro-3,3'-azobenzenedicarboxylic acid
• 英文别名: 5-[(3-Carboxy-4-chlorophenyl)diazenyl]-2-chlorobenzoic acid
• 化学式: C₁₄H₈Cl₂N₂O₄
• 分子量: 339.135
• InChiKey: LPOAZEZQTCACSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 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：
  99.3
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4'-dichloro-3,3'-azobenzenedicarboxylic acid 在 氯化亚砜 、 三乙胺 作用下， 反应 12.0h， 生成 4,4'-dichloroazobenzene-3,3'-dicarboxylic acid chloride
  参考文献：
  名称：

  Xiong, Chuan-Xi; Niu, Yong-Sheng; Zhou, Wei, Journal of Chemical Research, 2006, # 2, p. 139 - 140

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯-5-硝基苯甲酸 在 葡萄糖 、 sodium hydroxide 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 8.5h， 生成 4,4'-dichloro-3,3'-azobenzenedicarboxylic acid
  参考文献：
  名称：

  Qiu, Ming Yan; Zhang, Ji Chang; Shi, Wei Yun, Asian Journal of Chemistry, 2012, vol. 24, # 5, p. 2295 - 2297

  摘要：

  DOI：

文献信息

• Xiong, Chuan-Xi; Niu, Yong-Sheng; Zhou, Wei, Journal of Chemical Research, 2006, # 2, p. 139 - 140
  作者：Xiong, Chuan-Xi、Niu, Yong-Sheng、Zhou, Wei、Dong, Li-Jie

  DOI：——

  日期：——
• Qiu, Ming Yan; Zhang, Ji Chang; Shi, Wei Yun, Asian Journal of Chemistry, 2012, vol. 24, # 5, p. 2295 - 2297
  作者：Qiu, Ming Yan、Zhang, Ji Chang、Shi, Wei Yun、Jia, Qing Chao、Niu, Yong Sheng

  DOI：——

  日期：——
• Five metal–organic frameworks based on isomeric chloro-functionalized azobenzenedicarboxylic acids
  作者：Mürsel Arıcı

  DOI：10.1016/j.poly.2018.08.018

  日期：2018.11

  Chloro-functionalized azobenzenedicarboxylic acids were prepared and their 2D and 3D metal-organic frameworks (MOFs), namely [Co(4,4'-Cl(2)abdc)(DMA)]center dot H2O}(n) (1), [Cu(4,4'-Cl(2)abdc)(DMA)]center dot G}(n), (2), [Zn(4,4'-Cl(2)abdc)(DMSO)center dot H2O}(n) (3), [Mn(3,3'-Cl(2)abdc)(DMA)]center dot 0.5DMA)](n) (4) and ([Cu(3,3'-Cl(2)abdc)(DMA)]center dot 0.5DMA)(n) (5), (4,4'-H(2)Cl(2)abdc: 3,3'-dichloro-4,4'-azobenzenedicarboxylic acid, 3,3'-H(2)Cl(2)abdc: 4,4'-dichloro-3,3'-azobenzenedicarboxylic acid), were systematically synthesized to investigate the positional isomer effect on the structures and characterized by elemental analysis, IR spectroscopy and single crystal X-ray diffraction. The X-ray results demonstrate that 1 and 3 possess a 2-fold interpenetrated 3D + 3D -> 3D framework with the seh-4,6-Imma topology, while 2, 4 and 5 display 2D layers. In 1 and 3, infinite [M2O(COO)(2)] rod units occur, whilst well-known binuclear [M-2(COO)(4)] units are observed in the other compounds. Compounds 4 and 5 display a lower dimension due to the cis-position of the carboxylate groups of 3,3'-Cl(2)abdc as compared to compounds 1-3, prepared with 4,4'-Cl(2)abdc. Moreover, the thermal, photoluminescence and optical properties of the compounds were also examined. (C) 2018 Elsevier Ltd. All rights reserved.