(4-bromophenyl)-pyridin-4-yldiazene | 20815-54-7

• 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-bromophenyl)-pyridin-4-yldiazene
• 英文别名: (E)-1-pyridyl-2-[4-(bromo)phenyl]diazene；(4-bromophenyl)-pyridin-4-yl-diazene；4-(4-bromo-phenylazo)-pyridine；4-(4-Brom-phenylazo)-pyridin
• CAS: 20815-54-7
• 化学式: C₁₁H₈BrN₃
• 分子量: 262.109
• InChiKey: KGYKCSWSZUCLLB-CCEZHUSRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.26
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  (4-bromophenyl)-pyridin-4-yldiazene 在 氢溴酸 、 溶剂黄146 作用下， 生成 N-(2,4-dibromo-phenyl)-N'-[4]pyridyl-hydrazine
  参考文献：
  名称：

  Koenigs et al., Chemische Berichte, 1926, vol. 59, p. 324

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydroxide 作用下， 生成 (4-bromophenyl)-pyridin-4-yldiazene
  参考文献：
  名称：

  Koenigs et al., Chemische Berichte, 1926, vol. 59, p. 324

  摘要：

  DOI：

文献信息

• Hierarchical Synthesis, Structure, and Photophysical Properties of Gallium‐ and Ruthenium‐Porphyrins with Axially Bonded Azo Ligands
  作者：Yueze Gao、Vroni Walter、Michael J. Ferguson、Rik R. Tykwinski

  DOI：10.1002/chem.202002030

  日期：2020.12.15

  The hierarchical synthesis of three porphyrin and four bisporphyrin derivatives is presented. This strategy relies on the incorporation of linkers based on azo moieties appended with pyridyl and/or acetylenic groups that facilitate axial coordination to Ga‐ and Ru‐metalloporphyrins. These porphyrinic systems allow for a quantitative analysis of the effects of diamagnetic anisotropy (DA) by using 1H NMR

  介绍了三种卟啉和四种双卟啉衍生物的分级合成。该策略依赖于结合基于偶氮基的连接基，并附加有吡啶基和/或炔属基团，这些基团有利于Ga-和Ru-金属卟啉的轴向配位。这些卟啉系统可通过1 H NMR光谱和X射线晶体学分析对抗磁各向异性（DA）的影响进行定量分析。实验概述了质子化学位移和与卟啉核的距离之间的简单幂律关系，这证实了先前的理论预测，并表明DA的极限约为2 nm。偶氮连接的卟啉的光物理性质通过紫外/可见光谱分析，表明明显的顺式–仅与Ga卟啉结合的偶氮配体未观察到反式异构化。Ru-卟啉与偶氮配体的结合有利于光开关行为，但该过程面临Ru-卟啉脱羰作用的竞争，只有GaL1Ru记录了明显的开关。
• From Azobenzene Coordination to Aryl−Halide Bond Activation by Platinum
  作者：Olena Zenkina、Marc Altman、Gregory Leitus、Linda J. W. Shimon、Revital Cohen、Milko E. van der Boom

  DOI：10.1021/om700519v

  日期：2007.8.1

  This contribution describes the reactivity of Pt(PEt3)(4) with (4-bromo-phenyl)-pyridin-4-yl-diazene. eta(2)-Coordination of Pt(PEt3)(2) to the NN moiety is kinetically preferable and followed by an aryl-halide bond activation process. This quantitative transformation proceeds under mild reaction conditions in solution and in the solid state. Mechanistic studies in solution indicate that the metal insertion into the aryl-halide bond is the rate-determining step. The reaction obeys first-order kinetics in the eta(2)-coordination complex with Delta G(298K) = 24.6 +/- 1.6 kcal/mol, Delta H = 26.5 +/- 1.6 kcal/mol, and Delta S = 6.6 +/- 5.0 eu. No effect on the reaction progress and NMR line shape has been observed in the presence of excess PEt3. However, competition experiments with the eta(2)-coordination complex and PhBr reveal that the product ratio can be altered by the presence of PEt3, indicating that the two aryl-halide bond activation processes proceed via different mechanistic pathways. Numerical analysis of a series of competition experiments fits a reaction scheme involving a unimolecular transformation from the eta(2)-coordination complex to the product of aryl-halide oxidative addition. This "ring-walking" process is kinetically accessible as shown by density functional theory (DFT) calculations at the PCM:PBE0/SDB-cc-pVDZ/PBE0/SDD level of theory.