4,4'-dibromoazobenzene N,N'-dioxide | 57574-08-0

• 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: 4,4'-dibromoazobenzene N,N'-dioxide
• 英文别名: (E)-bis-(4-bromo-phenyl)-diazene-N,N'-dioxide；(E)-Bis-(4-brom-phenyl)-diazen-N,N'-dioxid；(E)-4,4'-Dibromoazoxybenzene-N-oxide；(E)-(4-bromophenyl)-[(4-bromophenyl)-oxidoazaniumylidene]-oxidoazanium
• CAS: 57574-08-0
• 化学式: C₁₂H₈Br₂N₂O₂
• 分子量: 372.016
• InChiKey: SJDLUMBUMZLHMX-FOCLMDBBSA-N

物化性质

• 沸点：
  465.1±55.0 °C(Predicted)
• 密度：
  1.811±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 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：
  57.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4'-dibromoazobenzene N,N'-dioxide 反应 9.0h， 生成 1-溴-4-亚硝基苯
  参考文献：
  名称：

  Solid-State Reaction Mechanisms in Monomer−Dimer Interconversions of p-Bromonitrosobenzene. Single-Crystal-to-Single-Crystal Photodissociation and Formation of New Non-van der Waals Close Contacts

  摘要：

  Thermal and photochemical reactions and the phase transition mechanisms of solid-state monomer-dimer interconversions of p-bromonitrosobenzene were studied on the basis of kinetics data and single-crystal-to-single-crystaI transformations. From the crystal structure and packing of pbromobenzeneazodioxide and the previously determined structure of the freshly sublimed monomer, we have explained both consecutive steps in thermal dimerization. While the first reaction (formation of the metastable dimer) with first-order kinetics affords diminishing of the (2 2 0) critical crystal plane that intersects atoms of the nitroso groups, the second phase transformation step includes four critical planes, which show sigmoid kinetics. In the new phase growth, these crystal planes developed in two (Cartesian) dimensions as vectors perpendicular to ab and ac planes, which is in agreement with the dimensionality previously determined on the basis of the Avrami-Erofeyev analysis (with m = 2.01). Photochromic dissociation of the azodioxide at 100 K was followed by structure determination of the single-crystal-to-single-crystaI transformation. A new metastable monomer was discovered, in which, despite bond breaking, the nitrogen atoms of the neighboring monomers remained very close to each other (2.30 angstrom), i.e., 23.3% closer than is the sum of two N-atom van der Waals radii. Such an extraordinary close contact was also observed between N and 0 atoms. This tight packing can explain why the return to dimerization after the low temperature photodissociation occurs so rapidly at a temperature as low as 170 K.

  DOI：

  10.1021/jo051236u
• 作为产物：
  描述：

  1-溴-4-亚硝基苯 反应 0.5h， 生成 4,4'-dibromoazobenzene N,N'-dioxide
  参考文献：
  名称：

  亚硝基苯二聚化作为研究固态反应机理的模型系统

  摘要：

  通过使用对位取代的亚硝基苯作为模型化合物，研究了固态亚硝基化合物的热二聚作用。在FT-IR光谱动力学，时间分辨粉末衍射和低温X射线结构测定的基础上，提出了一种包括拓扑化学反应轨迹和相转移相互作用的机理。根据基于Avrami模型分析的动力学曲线形状，发现相转移可能是由对位取代的亚硝基苯与偶氮二氧化物的二聚反应触发的，而二聚反应又可能是由不同的填充因子引起的，例如起始亚硝基单体晶体无序。由于所代表的模型可以扩展到广泛的化合物系列，

  DOI：

  10.1021/jo049537b