4-(4-硝基苯基偶氮)苯胺 | 114090-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 中文名称: 4-(4-硝基苯基偶氮)苯胺
• 英文名称: 4-(4-nitrophenylazo)phenylamine
• 英文别名: 4,4'-nitro-aminoazobenzene；cis-4-(4-nitrophenylazo)aniline；cis-4-nitro-4'aminoazobenzene；p-(p-Nitrophenylazo)-anilin
• CAS: 114090-39-0
• 化学式: C₁₂H₁₀N₄O₂
• 分子量: 242.237
• InChiKey: UNBOSJFEZZJZLR-PFONDFGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.88
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(4-硝基苯基偶氮)苯胺 以 正庚烷 为溶剂， 生成 disperse orange 3
  参考文献：
  名称：

  Rate constants of the thermal cis-trans isomerization of azobenzene dyes in solvents, acetone/water mixtures, and in microheterogeneous surfactant solutions

  摘要：

  Rate constants k(iso) of the thermal cis-trans isomerization of four 4,4'-nitro-aminoazobenzenes with different amino groups have been determined in homogeneous aprotic solvents and polyglykol oligomers, primarily by means of conventional flash photolysis. The rate constants have been correlated with polarity (according to lambda(max) from UV/Vis absorption spectra of the trans isomers) and bulk viscosity of the solvents. Qualitative conclusions about the influence of varying concentrations of water with respect to polarity and hydrogen banding on k(iso)- and lambda(max)-values in acetone/water mixtures were derived. Based on these results the data from microheterogeneous solutions have been interpreted.In microheterogeneous water/surfactant solutions k(iso)-values of selected azo dyes were strongly dependent on the concentrations of SDS, Triton(R) X-100, C12EO8 in water, and varied with the composition of bicontinuous microemulsions of Igepal(R) CA-520/ heptane/water. The large spread of isomerization rate constants is in part due to varying microviscosity.Replacement of H2O by D2O in aqueous surfactant solutions produced surprisingly large kinetic solvent isotope effects. (C) 1999 John Wiley & Sons, Inc.

  DOI：

  10.1002/(sici)1097-4601(1999)31:5<337::aid-kin3>3.0.co;2-e
• 作为产物：
  描述：

  disperse orange 3 以 正庚烷 为溶剂， 生成 4-(4-硝基苯基偶氮)苯胺
  参考文献：
  名称：

  环境对不对称偶氮苯衍生物动力学和电子结构的影响——实验和量子化学计算

  摘要：

  摘要 用分光光度法测量了溶解在各种极性溶剂中的不对称取代偶氮苯的热驱动顺反异构化动力学。在 4-硝基-4'-氨基偶氮苯和 4-硝基-4'甲氧基偶氮苯中观察到溶剂化变色效应。该实验补充了量子化学计算。使用量子力学朗之万偶极子/蒙特卡罗 (QM/LD/MC) 方法考虑了溶剂效应。已在状态总和 (SOS) 方法中计算了所研究分子的一阶超极化张量。这两种方法都在全价方法 GRINDOL 中实现。

  DOI：

  10.1016/s0022-2860(01)00457-4

文献信息

• Synthesis and physico-chemical properties of highly conjugated azo-aromatic systems. 4-(azulen-1-yl)-pyridines with mono- and bis azo-aromatic moieties at C3-position of azulene
  作者：Alexandru C. Razus、Simona Nica、Liliana Cristian、Matei Raicopol、Liviu Birzan、Andreea Eugenia Dragu

  DOI：10.1016/j.dyepig.2011.02.008

  日期：2011.10

  Highly conjugated azo-aromatic systems have been prepared in high to moderate yields by linking mono- and bis-azo aromatic fragments to 4-(Rn-azulen-1-yl)-2,6-dimethyl-pyridine. The synthesized pi-extended systems have been studied by NMR spectroscopy, UV-Vis and electrochemistry. Systematic increase of the conjugation along the azobenzene skeleton has affected the spectral properties of the azophenyl substituted 4-(azulen-1-yl)-pyridine. The synthesized compounds exhibit a bathochromic shift of the visible absorption maxima with the increase of the conjugating skeleton and introduction of an electron-withdrawing group. The electrochemical behavior revealed a high stability toward oxidation owing to the higher polarization induced by the azulenylpyridine moiety. (C) 2011 Elsevier Ltd. All rights reserved.