2-((2-ethynylphenyl)ethynyl)quinoline | 1614261-90-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-((2-ethynylphenyl)ethynyl)quinoline
• CAS: 1614261-90-3
• 化学式: C₁₉H₁₁N
• 分子量: 253.303
• InChiKey: VPTVKMKWOLFLDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.62
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,2-二碘四氟苯 、 2-((2-ethynylphenyl)ethynyl)quinoline 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 22.0h， 以47%的产率得到2-((2-((2,3,4,5-tetrafluoro-6-iodophenyl)ethynyl)phenyl)ethynyl)-quinoline
  参考文献：
  名称：

  Intramolecular Halogen Bonding Supported by an Aryldiyne Linker

  摘要：

  Intramolecular halogen bonds between aryl halide donors and suitable acceptors, such as carbonyl or quinolinyl groups, held in proximity by 1,2-aryldiyne linkers, provide triangular structures in the solid state. Aryldiyne linkers provide a nearly ideal template for intramolecular halogen bonding as minor deviations from alkyne linearity can accommodate a variety of halogen bonding interactions, including O center dot center dot center dot Cl, O center dot center dot center dot Br, O center dot center dot center dot I, N center dot center dot center dot Br, and N center dot center dot center dot I. Halogen bond lengths for these units, observed by single crystal X-ray crystallography, range from 2.75 to 2.97 angstrom. Internal bond angles of the semirigid bridge between halogen bond donor and acceptor are responsive to changes in the identity of the halogen, the identity of the acceptor, and the electronic environment around the halogen, with the triangles retaining almost perfect co-planarity in even the most strained systems. Consistency between experimental results and structures predicted by M06-2X/6-31G* calculations demonstrates the this computational method for modeling halogen-bonded structures of this type. efficacy of

  DOI：

  10.1021/jo501015x
• 作为产物：
  描述：

  2-((2-bromophenyl)ethynyl)quinoline 在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 25.0h， 生成 2-((2-ethynylphenyl)ethynyl)quinoline
  参考文献：
  名称：

  Intramolecular Halogen Bonding Supported by an Aryldiyne Linker

  摘要：

  Intramolecular halogen bonds between aryl halide donors and suitable acceptors, such as carbonyl or quinolinyl groups, held in proximity by 1,2-aryldiyne linkers, provide triangular structures in the solid state. Aryldiyne linkers provide a nearly ideal template for intramolecular halogen bonding as minor deviations from alkyne linearity can accommodate a variety of halogen bonding interactions, including O center dot center dot center dot Cl, O center dot center dot center dot Br, O center dot center dot center dot I, N center dot center dot center dot Br, and N center dot center dot center dot I. Halogen bond lengths for these units, observed by single crystal X-ray crystallography, range from 2.75 to 2.97 angstrom. Internal bond angles of the semirigid bridge between halogen bond donor and acceptor are responsive to changes in the identity of the halogen, the identity of the acceptor, and the electronic environment around the halogen, with the triangles retaining almost perfect co-planarity in even the most strained systems. Consistency between experimental results and structures predicted by M06-2X/6-31G* calculations demonstrates the this computational method for modeling halogen-bonded structures of this type. efficacy of

  DOI：

  10.1021/jo501015x

文献信息

• Comparing Strong and Weak Halogen Bonding in Solution: ¹³ C NMR, UV/Vis, Crystallographic, and Computational Studies of an Intramolecular Model
  作者：Danielle L. Widner、Emily R. Robinson、Alejandra B. Perez、Herh G. Vang、Rachel A. Thorson、Zakarias L. Driscoll、Sierra M. Giebel、Calvin W. Berndt、Eric Bosch、Erin D. Speetzen、Nathan P. Bowling

  DOI：10.1002/ejoc.201700969

  日期：2017.10.17

  Electron-withdrawing fluorine groups are commonly installed near halogen-bond donors to increase Lewis acidity. Are these substituents necessary, however, when the halogen-bond donor and acceptor are connected by an aryldiyne linker?

  吸电子的氟基团通常安装在卤素键供体附近，以提高路易斯酸度。但是，当卤素键供体和受体通过芳基二炔连接基连接时，这些取代基是否必要？