2-Amino-5-[[4-(4-amino-3-carboxyphenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]benzoic acid | 1239685-08-5

• 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: 2-Amino-5-[[4-(4-amino-3-carboxyphenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]benzoic acid
• CAS: 1239685-08-5；1328078-28-9；1328080-55-2
• 化学式: C₂₀H₁₆N₄O₄
• 分子量: 376.371
• InChiKey: ZHQBGLRCFUXNMZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  151
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  邻氨基苯甲酸 、 对苯二胺 在 盐酸 、 ammonium peroxydisulfate 作用下， 以 水 为溶剂， 生成 2-Amino-5-[[4-(4-amino-3-carboxyphenyl)iminocyclohexa-2,5-dien-1-ylidene]amino]benzoic acid
  参考文献：
  名称：

  DFT and experimental study of N,N′-bis(3′-carboxy,4′-aminophenyl)-1,4-quinonediimine, a carboxyl substituted aniline trimer

  摘要：

  Density functional calculations were performed on N,N'-bis(3'-carboxy,4'-aminophenyl)-1,4-quinonediimine, a carboxylic acid substituted aniline trimer. Results of the calculations were compared to experimental properties of the herein synthesized trimer, as well as to the properties of the anthranilic acid/aniline co-polymer reported in the literature. The calculated LUMO levels for isomers of the title compound range from -4.45 to -5.05 eV. The calculated electron affinities range from 75.93 kcal mol(-1) to 89.04 kcal mol(-1) (3.29-3.86 eV). Both the LUMO levels and electron affinities are greatest in magnitude for the anti, syn isomer. The HOMO levels, on the other hand, range from -5.32 eV (for the trans, trans isomer) to -5.36 eV (syn, syn inner). In acetonitrile solvent, the zwitterionic form is calculated to be energetically preferred to the non-zwitterion. Experimental UV-vis and near-IR studies in acetonitrile and ethanol show little evidence for zwitterion formation, but those in water show strong evidence. The predicted electronic transitions for the non-zwitterion in acetonitrile solvent correspond closely to those seen at 533 and 416 nm. The zwitterion present in solvent corresponds to a trimer with the capability to "self-dope", suggesting that the trimer would be effective at corrosion inhibition in the emeraldine base form, unlike other trimers which are only effective in the emeraldine salt form. This effectiveness in the emeraldine base form would enable the material to be utilized in corrosion inhibition applications in alkaline environments where standard oligo- and polyanilines fail. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2010.05.038