1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide compound with 1,4-diazabicyclo[2.2.2]octane (1:1) | 1379459-88-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: 1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide compound with 1,4-diazabicyclo[2.2.2]octane (1:1)
• 英文别名: [HDABCO][TFSA]
• CAS: 1379459-88-7
• 化学式: C₂HF₆NO₄S₂*C₆H₁₂N₂
• 分子量: 393.331
• InChiKey: ZRBLSOWEJTXDIS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.79
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  三乙烯二胺 、 双三氟甲烷磺酰亚胺 以 水 为溶剂， 以98.5%的产率得到1,1,1-trifluoro-N-((trifluoromethyl)sulfonyl)methanesulfonamide compound with 1,4-diazabicyclo[2.2.2]octane (1:1)
  参考文献：
  名称：

  基于手性Dabco衍生物（Dabco ＝ 1，4-二氮杂双环[2.2.2]辛烷）的高Tc对映体铁电体。

  摘要：

  1,4-二氮杂双环[2.2.2]辛烷（dabco）及其衍生物已被广泛用作优秀分子铁电体的构建单元，已有数十年的历史。但是，基于达巴科的同手性铁电体仍然是空白。在此，通过在非铁电性[H 2 dabco] [TFSA] 2（TFSA =双（三氟甲基磺酰基）铵）的[H 2 dabco] 2+中加入甲基（Me）基并引入同手性，我们成功设计了对映体铁电体[ R和S -2-Me-​​H 2 dabco] [TFSA] 2。两种对映体在转变温度（T c）高达405.8 K和415.8 K，这在基于dabco的铁电体和同手性铁电体中都很出色。据我们所知，[ R和S -2-Me-​​H 2 dabco] [TFSA] 2是基于dabco的同手性铁电体的首例。这一发现为构建基于dabco的同手性铁电体开辟了道路，并将激发对更杰出的对映体分子铁电体的探索。

  DOI：

  10.1002/anie.202007660

文献信息

• Is Amine a Stronger Base in Ionic Liquid Than in Common Molecular Solvent? An Accurate Basicity Scale of Amines
  作者：Chong Mao、Zhen Wang、Pengju Ji、Jin-Pei Cheng

  DOI：10.1021/acs.joc.5b01200

  日期：2015.8.21

  The equilibrium basicities of 21 frequently used amines in two room-temperature ionic liquids (RTILs) were measured precisely. The standard deviation was much superior to that sparsely reported elsewhere. The data comparisons revealed that amines are stronger bases in ionic ligquids than in DMSO and water but weaker base than in acetonitrile (AN). Interestingly, regression analyses demonstrate that

  精确测量了两种室温离子液体（RTIL）中21种常用胺的平衡碱性。标准差比其他地方稀疏报道的要好得多。数据比较显示，胺在离子液体中比在DMSO和水中更强，但比乙腈（AN）更弱。有趣的是，回归分析表明，在两个RTIL中获得的碱度等级与AN中的关联性很好，而与水和DMSO中的碱度关联性很好。
• Redox and Acid-Base Properties of Binuclear 4-Terphenyldithiophenolate Complexes of Nickel
  作者：Felix Koch、Andreas Berkefeld、Hartmut Schubert、Claudius Grauer

  DOI：10.1002/chem.201603060

  日期：2016.10.4

  This work reports on the redox and acid–base properties of binuclear complexes of nickel from 1,4‐terphenyldithiophenol ligands. The results provide insight into the cooperative electronic interaction between a dinickel core and its ligand. Donor/acceptor contributions flexibly adjust to stabilize different redox states at the metals, which is relevant for redox reactions like proton reduction. Proton

  这项工作报告了来自1,4-叔苯基二硫代苯酚配体的镍双核络合物的氧化还原和酸碱性质。结果提供了对双镍核及其配体之间的协同电子相互作用的见解。供体/受体的贡献可以灵活地调整，以稳定金属上的不同氧化还原态，这与氧化还原反应（如质子还原）有关。质子传递到[S 2 Ni 2 ]核和Ni-H键的形成在动力学上优于热力学上有利但无用的质子传递到配体上。
• The 1 : 1 and 1 : 2 salts of 1,4-diazabicyclo[2.2.2]octane and bis(trifluoromethylsulfonyl)amine: thermal behaviour and polymorphism
  作者：Gerhard Laus、Michael Hummel、Daniel M. Többens、Thomas Gelbrich、Volker Kahlenberg、Klaus Wurst、Ulrich J. Griesser、Herwig Schottenberger

  DOI：10.1039/c1ce05310h

  日期：——

  The salts of 1,4-diazabicyclo[2.2.2]octane (DABCO) and bis(trifluoromethylsulfonyl)amine (in 1 : 1 and 1 : 2 stoichiometry, 1 and 2, respectively) were investigated by DSC, TGA, PXRD and single crystal X-ray diffraction. Thermal analysis of the two compounds revealed reversible phase transitions, indicating enantiotropic relationships between all the polymorphs. Compound 1 can exist as a room-temperature form 1L and as a high-temperature modification 1H. By contrast, 2 forms a low- (2L), an intermediate- (2I) and a high-temperature (2H) polymorph. The structures of 1L and 2L were determined by single crystal X-ray crystallography. N–H⋯O bonded cations of 1L are arranged in a staggered fashion and form infinite chains. The crystal contains two sets of symmetry related H-bonded chains, which are in an inclined orientation relative to one another. In the structure of 2L, the cation is N–H⋯O bonded to two neighbouring triflimide anions. The discrete H-bonded structure fragments resulting from these interactions assemble to a layer structure. The structure determination of the high-temperature forms 1H and 2H from PXRD data was negatively affected by a high degree of disorder of the triflimide anions. All N–H⋯O bonded DABCO chains in 1H adopt a parallel orientation, which is in contrast to the inclined orientation found in 1L.

  通过 DSC、TGA、PXRD 和单晶 X 射线衍射，研究了 1,4-二氮杂双环[2.2.2]辛烷 (DABCO) 和双(三氟甲基磺酰基)胺（分别为 1:1 和 1:2）的盐。这两种化合物的热分析显示出可逆的相变，表明所有多晶体之间存在对映关系。化合物 1 可以室温形式 1L 和高温形式 1H 存在。相比之下，化合物 2 可形成低温（2L）、中温（2I）和高温（2H）多晶型。1L 和 2L 的结构是通过单晶 X 射线晶体学确定的。1L 的 NâHâ¯O 键阳离子交错排列，形成无限链。晶体中包含两组对称性相关的 H 键链，这两组 H 键链相互之间呈倾斜方向。在 2L 的结构中，阳离子以 NâHâ¯O 键与两个相邻的三亚甲基阴离子结合。这些相互作用产生的离散 H 键结构片段组合成层状结构。根据 PXRD 数据确定高温形式 1H 和 2H 的结构受到了三氟甲基阴离子高度无序性的负面影响。1H 中的所有 NâHâ¯O 键 DABCO 链都呈平行取向，这与 1L 中的倾斜取向形成了鲜明对比。
• Bistable State of Protons for Low-Voltage Memories
  作者：Xian-Jiang Song、Zhi-Xu Zhang、Xiao-Gang Chen、Han-Yue Zhang、Qiang Pan、Jie Yao、Yu-Meng You、Ren-Gen Xiong

  DOI：10.1021/jacs.0c02924

  日期：2020.5.13

  Molecular ferroelectrics are attracting tremendous interest because of their easy and environmental-friendly processing, low acoustic impedance, and mechanical flexibility. Their ferroelectric mechanism is mainly ascribed to the order-disorder transition of molecules such as spherical 1,4-diazabicyclo [2.2.2] octane (DABCO) and quinuclidine. Here, we present two molecular ferroelectrics, [HDABCO] [TFSA] and its deuterated one [DDABCO][TFSA] (TFSA = bis(trifluoromethylsulfonyl)ammonium), whose ferroelectricity is triggered by the proton ordering. This is the first time that the protons show a thermally fluctuated bistability with a double-well potential in DABCO-based ferroelectrics. A large deuterium isotope effect (Delta T = similar to 53 K) not only proves that they are hydrogen-bonded ferroelectrics but also extends the ferroelectric working temperature range to room temperature. The superfast polarization switching of 100 kHz and ultralow coercive voltage of 1 V (far less than 5 V required for commercially available ferroelectric devices), benefiting from the low energy for proton transfer, allow [DDABCO][TFSA] a great potential for memory devices with low-voltage, high-speed operation. This work should inspire further exploration of hydrogen-bonded molecular ferroelectrics for flexible and wearable devices with the low-power information storage.