1,2-bis(3-azidophenyl)acetylene | 134682-47-6

• 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: 1,2-bis(3-azidophenyl)acetylene
• 英文别名: 1-Azido-3-[2-(3-azidophenyl)ethynyl]benzene
• CAS: 134682-47-6
• 化学式: C₁₄H₈N₆
• 分子量: 260.258
• InChiKey: QINPVTXWSYXFDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-bis(3-azidophenyl)acetylene 以 2-甲基四氢呋喃 为溶剂， 生成 、
  参考文献：
  名称：

  Iwamura, Hiizu; Murata, Shigeru, Molecular Crystals and Liquid Crystals (1969-1991), 1989, vol. 176, p. 33 - 48

  摘要：

  DOI：
• 作为产物：
  描述：

  3-硝基苯乙炔 在 吡啶 、 ammonium hydroxide 、 copper(l) iodide 、 sodium azide 、 硫酸 、 铁粉 、 溶剂黄146 、 sodium nitrite 作用下， 反应 5.33h， 生成 1,2-bis(3-azidophenyl)acetylene
  参考文献：
  名称：

  Magnetic interaction between the triplet centers in ethynylenebis(phenylnitrenes) and 1,3-butadiyne-1,4-diylbis(phenylnitrenes)

  摘要：

  The magnetic interaction of the two triplet phenylnitrene units linked together through an acetylene or a diacetylene linkage has been investigated by ESR spectroscopy. Two regioisomeric (meta,para' and meta,meta') diazides of 1,2-diphenylacetylene 12a and 1,4-diphenyl- 1,3-butadiyne 13a were prepared and photolyzed in a 2-methyltetrahydrofuran glass at 10 K to give the corresponding dinitrenes 12n and 13n. The m,p'-dinitrenes of 12n and 13n showed intense quintet signals which obeyed a Curie law in the temperature range 12-85 K. The m,m'-dinitrenes of 12n and 13n showed signals due to the thermally populated quintet states, the intensities of which reached a maximum at 50 and 28 K for 12n and 13n, respectively. It is concluded that the two remote phenylnitrene units in 12n and 13n interact sufficiently strongly through bonds to form quintet states that are concluded to be the ground state in the meta,para' isomers as predicted by theory. In the meta,meta' isomers, the quintet states are thermally populated from ground singlet states, the energy gaps between the two states (ca. 200 and 100 cal/mol for -C = C- and -C = C-C = C-, respectively) being dependent reasonably upon the distance between the two moieties. The results serve as good guiding principles for designing high-spin conjugated polymers with pendant radical centers.

  DOI：

  10.1021/ja00015a005

文献信息

• Discrete Self‐Assembled Metallo‐Foldamers with Heteroleptic Sequence Specificity
  作者：Dan Preston

  DOI：10.1002/anie.202108456

  日期：2021.9

  Discrete and structurally diverse foldamer sequences are constructed in both natural and abiotic systems primarily using inert connectivity with irreversible organic covalent bonds, serving to preserve the identity of the sequence. The formation of sequences under thermodynamic control using labile coordination bonds would be attractive for synthetic ease and modular capability, but this presents issues

  在天然和非生物系统中构建离散且结构多样的折叠体序列，主要使用惰性连接与不可逆的有机共价键，用于保持序列的身份。使用不稳定的配位键在热力学控制下形成序列对于合成的简易性和模块化能力来说很有吸引力，但这会带来有关序列保存的问题。这里介绍了一种将钯 (II) 金属离子整合到序列本身中的方法，通过在金属中心使用配体排列的互补配对来保持保真度。这是通过使用不同齿数和/或氢键能力的位点来实现的。以这种方式，离散和有序的金属序列在一步中形成为热力学产物，