6,6'-((5-(tert-butyl)-1,3-phenylene)bis(1H-1,2,3-triazole-1,4-diyl))bis(2-ethynylpyridine) | 1091631-66-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6,6'-((5-(tert-butyl)-1,3-phenylene)bis(1H-1,2,3-triazole-1,4-diyl))bis(2-ethynylpyridine)
• CAS: 1091631-66-1
• 化学式: C₂₈H₂₂N₈
• 分子量: 470.536
• InChiKey: ZGAIEJSETYPLEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  36.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  87.2
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3,5-diazido-1-(tert-butyl)benzene 、 6,6'-((5-(tert-butyl)-1,3-phenylene)bis(1H-1,2,3-triazole-1,4-diyl))bis(2-ethynylpyridine) 在 copper(l) iodide 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 17,35-Ditert-butyl-2,3,4,12,13,14,20,21,22,30,31,32,39,43-tetradecazanonacyclo[31.3.1.12,5.16,10.111,14.115,19.120,23.124,28.129,32]tetratetraconta-1(37),3,5(44),6(43),7,9,11(42),12,15(41),16,18,21,23(40),24,26,28(39),29(38),30,33,35-icosaene
  参考文献：
  名称：

  Dipole-Promoted and Size-Dependent Cooperativity between Pyridyl-Containing Triazolophanes and Halides Leads to Persistent Sandwich Complexes with Iodide

  摘要：

  Triazolophanes that incorporate pyridyl subunits in place of phenylenes show a heightened propensity to form 2:1 sandwich complexes with halides. Persistent iodide-based sandwiches are observed. Binding constants confirm that the inward-facing electron pairs on the pyridyls destabilize the 1:1 complexes with halides. The H-1 NMR spectra verify that the sandwich complexes have two TT-stacked triazolophanes rotated to allow registration between opposite dipoles on the pyridyls (directed inward) and triazoles (directed outward). These dipolar interactions cooperate to lower the pyridyl-based repulsions, therefore, increasing K-2. Modest cooperative effects are observed for the snugly fitting F-, Cl-, and Br- halides while the too-large l(-) shows highly positive cooperativity.

  DOI：

  10.1021/ja8077329
• 作为产物：
  描述：

  C₃₄H₃₈N₈Si₂ 在 甲醇 、 potassium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以92%的产率得到6,6'-((5-(tert-butyl)-1,3-phenylene)bis(1H-1,2,3-triazole-1,4-diyl))bis(2-ethynylpyridine)
  参考文献：
  名称：

  Dipole-Promoted and Size-Dependent Cooperativity between Pyridyl-Containing Triazolophanes and Halides Leads to Persistent Sandwich Complexes with Iodide

  摘要：

  Triazolophanes that incorporate pyridyl subunits in place of phenylenes show a heightened propensity to form 2:1 sandwich complexes with halides. Persistent iodide-based sandwiches are observed. Binding constants confirm that the inward-facing electron pairs on the pyridyls destabilize the 1:1 complexes with halides. The H-1 NMR spectra verify that the sandwich complexes have two TT-stacked triazolophanes rotated to allow registration between opposite dipoles on the pyridyls (directed inward) and triazoles (directed outward). These dipolar interactions cooperate to lower the pyridyl-based repulsions, therefore, increasing K-2. Modest cooperative effects are observed for the snugly fitting F-, Cl-, and Br- halides while the too-large l(-) shows highly positive cooperativity.

  DOI：

  10.1021/ja8077329