tris(2,6-difluorophenyl)boroxine | 1156464-25-3

• 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: tris(2,6-difluorophenyl)boroxine
• 英文别名: tris(2,6-difluorophenyl)boroxin；2,4,6-Tris(2,6-difluorophenyl)-1,3,5,2,4,6-trioxatriborinane
• CAS: 1156464-25-3
• 化学式: C₁₈H₉B₃F₆O₃
• 分子量: 419.691
• InChiKey: OZJIDZKKJRUVCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.07
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tetra-n-butylammoniumfluoride trihydrate 、 tris(2,6-difluorophenyl)boroxine 以 乙腈 为溶剂， 生成 tris(2,6-difluorophenyl)boroxin fluoride
  参考文献：
  名称：

  Fluorinated Boroxin-Based Anion Receptors for Lithium Ion Batteries: Fluoride Anion Binding, Ab Initio Calculations, and Ionic Conductivity Studies

  摘要：

  Novel fluorinated boroxines, tris(2,6-difluorophenyl)boroxin (DF), tris(2,4,6-trifluorophenyl)boroxin (TF), and tris(pentafluorophenyl)boroxin (PF), have been investigated for potential applications in lithium ion batteries through fluoride anion binding, ab initio calculations, and ionic conductivity measurements. Structures of the fluorinated boroxines and boroxin-fluoride complexes have been confirmed by comparing their F-19 and B-11 NMR chemical shifts with those obtained by the DFT-GIAO method. The stoichiometry of the fluoride anion binding to these boroxines has been shown to be 1:1 using F-19 NMR and UV-vis spectroscopy. UV-vis spectroscopic studies show the coexistence of more than one complex, in addition to the 1:1 complex, for perfluorinated boroxin, PF. DFT calculations (B3LYP/6-311G**) show that the fluoride ion complex of DF prefers unsymmetrical, covalently bound structure (7) over the symmetrically bridged species (10) by 12.5 kcal/mol. Rapid equilibration of the fluoride anion among the three borons in these boroxines results in a single F-19 NMR absorption for all of the aromatic ortho- or para-fluorines at ambient temperature. The effect of these anion receptors on lithium ion conductivities was also explored for potential applications in dual ion intercalating lithium batteries.

  DOI：

  10.1021/jp901952t
• 作为产物：
  描述：

  2,6-二氟苯硼酸 以 neat (no solvent) 为溶剂， 生成 tris(2,6-difluorophenyl)boroxine
  参考文献：
  名称：

  摘要：

  A general preparative procedure for polyfluorinated aryl(dihydroxy)boranes C6H5-nFnB(OH)(2) (n = 3 - 5) is described. Polyfluorinated aryl(dihydroxy)boranes are easily dehydrated to the corresponding tri(aryl)boroxins (C6H5-nFnBO)(3) by thermal or chemical treatment. The property of the acids C6H5-nFnB(OH)(2) to condensate depends on the number and on the position of the fluorine atoms in the aryl group. Examples of both classes of boron compounds were isolated as pure individuals and characterized by multinuclear NMR spectroscopy.

  DOI：

  10.1002/1521-3749(200213)628:13<2827::aid-zaac2827>3.0.co;2-n

文献信息

• ——
  作者：H.-J. Frohn、N. Y. Adonin、V. V. Bardin、V. F. Starichenko

  DOI：10.1002/1521-3749(200213)628:13<2827::aid-zaac2827>3.0.co;2-n

  日期：——

  A general preparative procedure for polyfluorinated aryl(dihydroxy)boranes C6H5-nFnB(OH)(2) (n = 3 - 5) is described. Polyfluorinated aryl(dihydroxy)boranes are easily dehydrated to the corresponding tri(aryl)boroxins (C6H5-nFnBO)(3) by thermal or chemical treatment. The property of the acids C6H5-nFnB(OH)(2) to condensate depends on the number and on the position of the fluorine atoms in the aryl group. Examples of both classes of boron compounds were isolated as pure individuals and characterized by multinuclear NMR spectroscopy.
• Fluorinated Boroxin-Based Anion Receptors for Lithium Ion Batteries: Fluoride Anion Binding, Ab Initio Calculations, and Ionic Conductivity Studies
  作者：Nanditha G. Nair、Mario Blanco、William West、F. Christoph Weise、Steve Greenbaum、V. Prakash Reddy

  DOI：10.1021/jp901952t

  日期：2009.5.21

  Novel fluorinated boroxines, tris(2,6-difluorophenyl)boroxin (DF), tris(2,4,6-trifluorophenyl)boroxin (TF), and tris(pentafluorophenyl)boroxin (PF), have been investigated for potential applications in lithium ion batteries through fluoride anion binding, ab initio calculations, and ionic conductivity measurements. Structures of the fluorinated boroxines and boroxin-fluoride complexes have been confirmed by comparing their F-19 and B-11 NMR chemical shifts with those obtained by the DFT-GIAO method. The stoichiometry of the fluoride anion binding to these boroxines has been shown to be 1:1 using F-19 NMR and UV-vis spectroscopy. UV-vis spectroscopic studies show the coexistence of more than one complex, in addition to the 1:1 complex, for perfluorinated boroxin, PF. DFT calculations (B3LYP/6-311G**) show that the fluoride ion complex of DF prefers unsymmetrical, covalently bound structure (7) over the symmetrically bridged species (10) by 12.5 kcal/mol. Rapid equilibration of the fluoride anion among the three borons in these boroxines results in a single F-19 NMR absorption for all of the aromatic ortho- or para-fluorines at ambient temperature. The effect of these anion receptors on lithium ion conductivities was also explored for potential applications in dual ion intercalating lithium batteries.