sodium tetrakis(3,5-bis(perfluorohexyl)phenyl)borate

• 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: sodium tetrakis(3,5-bis(perfluorohexyl)phenyl)borate
• 英文别名: Sodium;tetrakis[3,5-bis(1,1,2,2,3,3,4,4,5,5,6,6,6-tridecafluorohexyl)phenyl]boranuide
• 化学式: C₇₂H₁₂BF₁₀₄*Na
• 分子量: 2886.52
• InChiKey: ICAOUCBHXDSTGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  33.63
• 重原子数：
  178
• 可旋转键数：
  40
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  105

反应信息

• 作为反应物：
  描述：

  1,2,3,4,5,6,7,8-八氢吖啶 、 sodium tetrakis(3,5-bis(perfluorohexyl)phenyl)borate 在 盐酸 作用下， 以 水 、 正戊烷 为溶剂， 反应 2.08h， 生成
  参考文献：
  名称：

  气相和非质子溶剂中伦敦色散的补偿。

  摘要：

  近年来，伦敦分散体对于少于200个原子的分子的结构和稳定性的重要性已经确立，但由于持续缺乏合适的实验数据，对定量的理解仍主要基于计算。我们在此报告了质子结合的二聚体解离中伦敦色散补偿的综合计算和实验研究，结果表明，极性和非极性非质子溶剂中的总补偿在很大范围内都具有很大的不变性。此外，我们发现在典型的实验温度下，溶剂补偿（约40％至80％）比气相补偿（约0％至40％）在很大程度上占优势。

  DOI：

  10.1002/anie.201905436
• 作为产物：
  描述：

  3,4-bis(tridecafluoro-n-hexyl)bromobenzene 在 叔丁基锂 、 三氯化硼 、 sodium chloride 作用下， 以 乙醚 、 正戊烷 、 正己烷 、 溶剂黄146 为溶剂， 反应 1.0h， 以46%的产率得到sodium tetrakis(3,5-bis(perfluorohexyl)phenyl)borate
  参考文献：
  名称：

  四{3,5-双（全氟己基）苯基}硼酸酯：高氟阴离子

  摘要：

  为寻找使催化剂可溶于氟溶剂的新可能性，描述了四{3，5-双（全氟己基）苯基}硼酸硼酸钠的钠衍生物的制备，硼酸钠是一种新型的高氟阴离子。这种弱配位的阴离子对全氟化溶剂表现出显着的亲和力，因此有望与氟双相循环技术兼容的阳离子过渡金属催化剂种类繁多。

  DOI：

  10.1016/s0040-4039(01)01716-6

文献信息

• Tetrakis{3,5-bis(perfluorohexyl)phenyl}borate: a highly fluorous anion
  作者：Joep van den Broeke、Berth-Jan Deelman、Gerard van Koten

  DOI：10.1016/s0040-4039(01)01716-6

  日期：2001.11

  rendering catalysts soluble in fluorous solvents, the preparation of a sodium derivative of tetrakis3,5-bis(perfluorohexyl)phenyl}borate, a new and highly fluorous anion, is described. This weakly coordinating anion exhibits substantial affinity for perfluorinated solvents and is therefore expected to make a broad range of cationic transition-metal catalysts compatible with fluorous biphasic recycling

  为寻找使催化剂可溶于氟溶剂的新可能性，描述了四3，5-双（全氟己基）苯基}硼酸硼酸钠的钠衍生物的制备，硼酸钠是一种新型的高氟阴离子。这种弱配位的阴离子对全氟化溶剂表现出显着的亲和力，因此有望与氟双相循环技术兼容的阳离子过渡金属催化剂种类繁多。
• Different Modes of Anion Response Cause Circulatory Phase Transfer of a Coordination Cage with Controlled Directionality
  作者：Nozomi Mihara、Tanya K. Ronson、Jonathan R. Nitschke

  DOI：10.1002/anie.201906644

  日期：2019.9.2

  reported with controlled directionality between three phases, based on a cage that responds reversibly in two distinct ways to different anions. Notably, circulatory phase transfer of the cage was demonstrated based on a system where the three layers of solvent are arranged within a circular track. The direction of circulation between solvent phases depended upon the order of addition of anions.

  从细胞传输到有机体循环系统，分子的受控定向传输对于复杂的自然系统至关重要。与这些自然系统相反，当施加外部刺激时，能够在宏观尺度上的几个空间位置之间转移分子的合成系统仍有待探索。现在，据报道超分子笼的转移在三个相之间具有可控的方向性，这是基于一种笼，该笼以两种不同的方式对不同的阴离子可逆地响应。值得注意的是，基于三层溶剂排列在圆形轨道内的系统，证明了保持架的循环相转移。溶剂相之间的循环方向取决于阴离子的添加​​顺序。
• New Media for Classical Coordination Chemistry: Phase Transfer of Werner and Related Polycations into Highly Nonpolar Fluorous Solvents
  作者：Subrata K. Ghosh、Ann Sullivan Ojeda、Juan Guerrero-Leal、Nattamai Bhuvanesh、John A. Gladysz

  DOI：10.1021/ic400945u

  日期：2013.8.19

  Optimized procedures for the previously reported conversions of 1,3-diiodobenzene and perfluorohexyliodide (Rf6I; copper, DMSO, 140 degrees C) to 1,3-C6H4(R-f6)(2) (3; 86-70%) and 3 to Br(3,5-C6H3(R-f6)(2) (2; NBS, H2SO4/CF3CO2H; 88-75%) are described. The latter is converted (t-BuLi, BCl3) to the "fluorous BArf" salt NaB(3,5-C6H3(R-f6)(2))(4) (1 or NaBArf6; 77-70%), as given earlier. When orange aqueous solutions of [Co(en)(3)]Cl-3 (en = ethylenediamine) are treated with perfluoro(methylcyclohexane) (PFMC) solutions of 1 (1:3 mol ratio), the aqueous phase decolorizes and [Co(en)(3)](BArf6)(3) can be isolated from the fluorous phase (96%). Similar reactions with the trans-1,2-cyclohexanediamine analogue [Co(R,R-chxn)(3)]Cl-3 and [Ru(bipy)(3)]Cl-2 give [Co(R,R-chxn)(3)](BArf6)(3) (92%) and [Ru(bipy)(3)] (BArf6)(2) (95%). All of these salts are isolated as hydrates and exhibit toluene/PFMC partition coefficients of <= 1:>= 99, establishing that the anion BArf6- can efficiently transport polar polycations into highly nonpolar fluorous phases. When equal volumes of CH2Cl2 and PFMC are charged with the "nonfluorous" BArf (B(3,5-C6H3-(CF3)(2))(4)) salt [Co(en)(3)](BArf)(3) and 3.0 equiv of the fluorous salt NaBArf6, the cobalt trication partitions predominantly into the fluorous phase (64:36). The arene 2 crystallizes in a polar space group (tetragonal, I4, Z = 8) with fluorous and nonfluorous domains and all eight bromine atoms located essentially on one face of the unit cell.
• Compensation of London Dispersion in the Gas Phase and in Aprotic Solvents
  作者：Robert Pollice、Felix Fleckenstein、Ilya Shenderovich、Peter Chen

  DOI：10.1002/anie.201905436

  日期：2019.10

  importance of London dispersion for structure and stability of molecules with less than about 200 atoms has been established in recent years but the quantitative understanding is still largely based on computations because of a persistent lack of suitable experimental data. We herein report a comprehensive computational and experimental study of the compensation of London dispersion in proton-bound dimer

  近年来，伦敦分散体对于少于200个原子的分子的结构和稳定性的重要性已经确立，但由于持续缺乏合适的实验数据，对定量的理解仍主要基于计算。我们在此报告了质子结合的二聚体解离中伦敦色散补偿的综合计算和实验研究，结果表明，极性和非极性非质子溶剂中的总补偿在很大范围内都具有很大的不变性。此外，我们发现在典型的实验温度下，溶剂补偿（约40％至80％）比气相补偿（约0％至40％）在很大程度上占优势。
• Fluorous Bulk Membranes for Potentiometric Sensors with Wide Selectivity Ranges:  Observation of Exceptionally Strong Ion Pair Formation
  作者：Paul G. Boswell、Philippe Bühlmann

  DOI：10.1021/ja052403a

  日期：2005.6.1

  Potentiometric sensors based on fluorous membranes doped with a fluorophilic tetraphenylborate derivative are shown to have a remarkably wide range of selectivities that exceeds the selectivity range of conventional polymeric membranes by 8 orders of magnitude. The fluorous character of these sensing membranes explains the formation of ion pairs of unprecedented strength. Ion pair formation constants in perfluoroperhydrophenanthrene, as measured in this work, are on the order of 1020 and exceed previously reported values for ion pair formation in nonpolar solvents by 6 orders of magnitude. The low solubility of lipids in such fluorous phases makes them very promising for the reduction of biofouling.