4-Nitronitrosobenzene trans dimer | 149522-75-8

• 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: 4-Nitronitrosobenzene trans dimer
• 英文别名: bis-(4-nitro-phenyl)-diazene-N,N'-dioxide；Bis-(4-nitro-phenyl)-diazen-N,N'-dioxid；(E)-(4-nitrophenyl)-[(4-nitrophenyl)-oxidoazaniumylidene]-oxidoazanium
• CAS: 149522-75-8
• 化学式: C₁₂H₈N₄O₆
• 分子量: 304.219
• InChiKey: GWDWGXIHJJCFDB-BUHFOSPRSA-N

物化性质

• 沸点：
  552.2±60.0 °C(Predicted)
• 密度：
  1.546±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基苯胺 在 <ϖ-C5H5N(1+)(CH2)15CH3>34>(3-) 双氧水 作用下， 以 氯仿 为溶剂， 反应 2.0h， 以47%的产率得到4-Nitronitrosobenzene trans dimer
  参考文献：
  名称：

  Oxidation of aromatic amines with hydrogen peroxide catalyzed by cetylpyridinium heteropolyoxometalates

  摘要：

  Various substituted anilines 1 were selectively converted into the corresponding nitrosobenzenes 2 or nitrobenzenes 3 by oxidation with aqueous hydrogen peroxide catalyzed by heteropolyoxometalates. The oxidations of anilines 1 with 35% H2O2 catalyzed by peroxotungstophosphate (PCWP) at room temperature in chloroform under two-phase conditions afforded nitrosobenzenes 2 with high selectivity. When the same reactions were carried out at higher temperature (e.g., refluxing chloroform), nitrobenzenes 3 were obtained in good yields. The oxidation of aniline (1a) with dilute H2O2 catalyzed by PCWP (2 wt %) in an aqueous medium produced azoxybenzene (4a) with high selectivity. Phenylazoxyalkanes 7 were prepared by the first direct cooxidation of la in the presence of primary aliphatic amines 6. For example, the oxidation of a 1:2 mixture of 1a and hexylamine (6b) with 35 % H2O2 (6 equiv) in the presence of PCWP produced phenylazoxyhexane (7b) (51 %) along with a small amount of 4a (8 %). The reaction path for the conversion of anilines to azoxy-, nitroso-, and nitrobenzenes is described.

  DOI：

  10.1021/jo00066a012

文献信息

• Nitrosobenzene cross-dimerization: Structural selectivity in solution and in solid state
  作者：Ivana Biljan、Gorana Cvjetojevic、Vilko Smrecki、Predrag Novak、Gregor Mali、Janez Plavec、Darko Babic、Zlatko Mihalic、Hrvoj Vancik

  DOI：10.1016/j.molstruc.2010.05.034

  日期：2010.8

  Abstract Possibility of nitrosobenzenes to form dimeric molecular structures (azodioxides) is used as a model for intermolecular selectivity investigations in solution as well as in solid state. Cross-dimerization of different combinations of p- and m-substituted nitrosobenzene pairs was studied by variable temperature 1H NMR, solid-state NMR (CP MAS), IR, and ab initio calculations. It is evident that

  摘要 亚硝基苯形成二聚分子结构（偶氮二氧化物）的可能性被用作溶液和固态分子间选择性研究的模型。通过变温 1H NMR、固态 NMR (CP MAS)、IR 和 ab initio 计算研究了对和间取代亚硝基苯对的不同组合的交叉二聚。很明显，对亚硝基苯具有非选择性，因为它与所有研究的亚硝基苯伙伴形成二聚体。相反，对甲氧基亚硝基苯在大多数情况下不会形成二聚体。可以通过晶格中分子排列的影响来解释溶液中形成二聚体的能力与固态不同的证据。