5-[[4-(Phenylcarbamoylamino)phenyl]carbamoylamino]benzene-1,3-dicarboxylic acid | 957048-13-4

• 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: 5-[[4-(Phenylcarbamoylamino)phenyl]carbamoylamino]benzene-1,3-dicarboxylic acid
• 英文别名: 5-[[4-(phenylcarbamoylamino)phenyl]carbamoylamino]benzene-1,3-dicarboxylic acid
• CAS: 957048-13-4
• 化学式: C₂₂H₁₈N₄O₆
• 分子量: 434.408
• InChiKey: FBVFVKLJOCQTJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-[[4-(Phenylcarbamoylamino)phenyl]carbamoylamino]benzene-1,3-dicarboxylic acid 、 苯胺 在 吡啶 、 亚磷酸三苯酯 、 lithium chloride 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 以91%的产率得到N,N'-diphenyl-5-{3-[4-(3-phenylureido)-phenyl]-ureido}isophthalamide
  参考文献：
  名称：

  Colorimetric anion sensing by polyamide models containing urea-binding sites

  摘要：

  Novel colorimetric polyamide model compounds for anion-sensing applications are described. Light beige solutions of one of the models (M3) in DMSO develop a red to yellow-reddish colour upon addition of some anions, including OH-, F-, HC[image omitted], P[image omitted], AcO-, benzoate-, oxalate2- and p-toluenesulphonate-. In contrast, they remain unchanged in the presence of CH2ClC[image omitted], H2P[image omitted], CF3CO2-, Br-, methanesulphonate-, Cl- or I-. The reddish colour caused by the addition of basic anions is due to the deprotonation of the urea groups, while the yellowish colour corresponds to the modification of the electron density surrounding the urea group due to complexation. The development of the yellow colour of DMSO solutions of M3 upon addition of acetate ions and the disappearance of the red colour of solutions of M3/fluoride by the displacement of acetate ions can serve as a novel colorimetric assay for the titration of the acetate anion, with detection limits close to 1ppb. The host:guest stoichiometry (polyamide model compound:anion complexes) and the stability constants of complexes were determined by 1H NMR.

  DOI：

  10.1080/10610270903531549

文献信息

• Colorimetric anion sensing by polyamide models containing urea-binding sites
  作者：Noelia San-José、Ana Gómez-Valdemoro、Saturnino Ibeas、Félix Clemente García、Felipe Serna、José Miguel García

  DOI：10.1080/10610270903531549

  日期：2010.6.1

  Novel colorimetric polyamide model compounds for anion-sensing applications are described. Light beige solutions of one of the models (M3) in DMSO develop a red to yellow-reddish colour upon addition of some anions, including OH-, F-, HC[image omitted], P[image omitted], AcO-, benzoate-, oxalate2- and p-toluenesulphonate-. In contrast, they remain unchanged in the presence of CH2ClC[image omitted], H2P[image omitted], CF3CO2-, Br-, methanesulphonate-, Cl- or I-. The reddish colour caused by the addition of basic anions is due to the deprotonation of the urea groups, while the yellowish colour corresponds to the modification of the electron density surrounding the urea group due to complexation. The development of the yellow colour of DMSO solutions of M3 upon addition of acetate ions and the disappearance of the red colour of solutions of M3/fluoride by the displacement of acetate ions can serve as a novel colorimetric assay for the titration of the acetate anion, with detection limits close to 1ppb. The host:guest stoichiometry (polyamide model compound:anion complexes) and the stability constants of complexes were determined by 1H NMR.