4,5-ethylenedithio-4'-carbamoyltetrathiafulvalene | 251901-43-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基硫酯
• 英文名称: 4,5-ethylenedithio-4'-carbamoyltetrathiafulvalene
• 英文别名: 3-amido-3',4'-ethylenedithiotetrathiafulvalene；EDT-TTF-CONH2；2-(5,6-Dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-ylidene)-1,3-dithiole-4-carboxamide
• CAS: 251901-43-6
• 化学式: C₉H₇NOS₆
• 分子量: 337.557
• InChiKey: AYPOEAFTGHLVBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  195
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [nBu4N⁺]₂[BABCO][BABCO^-]₂ 、 4,5-ethylenedithio-4'-carbamoyltetrathiafulvalene 以 甲醇 、 乙腈 为溶剂， 反应 240.0h， 生成 (EDT-TTF-CONH₂)₂⁺[BABCO^-]
  参考文献：
  名称：

  分子导体和分子转子的结晶混合物的设计和评估

  摘要：

  结合分子电导率和分子机械领域的最新概念，我们着手设计一种晶体分子导体，该导体也具有分子转子。我们报告了具有常见 1,4-双（羧乙炔基）双环 [2.2.2] 辛烷 (BABCO) 功能转子的两种固体的结构、电子和物理性质以及动力学。一种，[nBu(4)N(+)](2)[BABCO][BABCO(-)](2)，是一种无色绝缘体，其中二羧酸与其两种单阴离子共轭碱共结晶。另一种是通过电结晶自组装，呈黑色、闪亮的针状，具有 (EDT-TTF-CONH(2))(2)(+) (EDT-TTF = 乙撑二硫四硫富瓦烯) 和阴离子 [BABCO (-)] 转子。使用变温 (5-300 K) 质子自旋晶格弛豫，(1)HT(1)(-1)，我们能够在 [nBu(4)N(+)](2)[BABCO][BABCO(-)](2) 中分配两种类型的布朗旋转器。我们表明中性 BABCO 组在 300 K 时具有 120 GHz

  DOI：

  10.1021/ja301484b
• 作为产物：
  描述：

  ethylenedithiotetrathiafulvalene acid chloride 在 氨 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以92%的产率得到4,5-ethylenedithio-4'-carbamoyltetrathiafulvalene
  参考文献：
  名称：

  The crystal chemistry of amide‐functionalized ethylenedithiotetrathiafulvalenes: EDT‐TTF‐CONRR′ (R, R′ = H, Me)

  摘要：

  本文描述了在TTF核心上直接官能化的乙烯基二硫代四硫富瓦烯（EDT-TTF）的制备，该官能团具有伯、仲或叔酰胺或酰肼官能团。本文报道了EDT-TTF-CO2H、EDT-TTF-CONH2、EDT-TTF-CONHMe和EDT-TTF-CONMe2的X射线晶体结构。这些官能化分子采用的固态结构似乎是氢键要求之间的折衷，氢键分别由OH、NH2、CH和CO基团提供和接受，而EDT-TTF部分的S·S·S范德华相互作用。TTF核心氢原子的活化，邻位于酰胺基，增强了其参与短C-H·O键的能力，从而产生在仲酰胺EDT-TTF-CONHMe中观察到的特征螯合R2R1(7)结构。

  DOI：

  10.1039/a902852h

文献信息

• (EDT-TTF-CONH₂)₆[Re₆Se₈(CN)₆], a Metallic Kagome-Type Organic−Inorganic Hybrid Compound:  Electronic Instability, Molecular Motion, and Charge Localization
  作者：Stéphane A. Baudron、Patrick Batail、Claude Coulon、Rodolphe Clérac、Enric Canadell、Vladimir Laukhin、Roberto Melzi、Pawel Wzietek、Denis Jérome、Pascale Auban-Senzier、Sylvain Ravy

  DOI：10.1021/ja0523385

  日期：2005.8.24

  with the 100 K triclinic crystal structure and band structure calculations. A sliding motion, within one out of the three (EDT-TTF-CONH2)2 dimers coupled to the [Re6Se8(CN6)(3-)*]/[Re6Se8(CN6)4-] proportion at any temperature, and the electronic ground state of the organic-inorganic hybrid material are analyzed on the basis of ESR, dc conductivity, 1H spin-lattice relaxation, and static susceptibility

  (EDT-TTF-CONH2)6[Re6Se8(CN)6]，空间群 R，由伯酰胺功能化的亚乙基二硫代四硫富瓦烯 EDT-TTF-CONH2 (E(1/2)1 = 0.49 V vs SCE) 电结晶制备CH3CN 中）和分子簇四阴离子 [Re6Se8(CN)6]4-（E(1/2) = 0.33 V vs CH3CN 中的 SCE），分别配备有氢键供体和氢键受体功能。它的 Kagome 拓扑结构对于任何基于 TTF 的材料都是前所未有的。在室温下观察到的金属态具有很强的二维特征，与 Kagome 晶格对称性相干，并且存在微量的 [Re6Se8(CN)6](3-)* 由电子自旋光谱确定。在大约 10 处观察到了朝向具有较小对称性的扭曲形式的 Kagome 拓扑结构的结构不稳定性。180K。低温结构与局部电绝缘电子基态相关，其磁化率由局部 S = 1/2 自旋的均匀链模型解释，与 100 K 三
• Directing the Structures and Collective Electronic Properties of Organic Conductors: The Interplay of π-Overlap Interactions and Hydrogen Bonds
  作者：Karine Heuzé、Marc Fourmigué、Patrick Batail、Enric Canadell、Pascale Auban-Senzier

  DOI：10.1002/(sici)1521-3765(19991001)5:10<2971::aid-chem2971>3.0.co;2-s

  日期：——

  The ethylenedithiotetrathiafulvalene (EDT-TTF) directly functionalized with a primary amido group, which is both a hydrogen bond donor and acceptor group, is prepared from the corresponding ester. The electron-donating ability of EDT-TTF-CONH2 (1), which is comparable to that of bisethylenedithiotetrathiofulvalene (BEDT-TTF) despite the presence of the electron-withdrawing amidic group, allows the successful electrocrystallization of air-stable cation radical salts. Two completely different salts are obtained with the isosteric AsF6- and ReO4- ions; the former has 6:1 stoichiometry, and the latter has 2:1 stoichiometry. Compound (1)(6)(AsF6) crystallizes in the P (3) over bar space group, and the three crystallographically independent donor molecules are linked to each other through a combination of N-H ... O and C-H ... O hydrogen bonds. This strong trimeric motif organizes around the AsF6- ion located on the (3) over bar axis, exemplifying the templating effect of the octahedral anion on the whole structure. The presence of a uniform spin chain, as identified in the crystal structure, is confirmed by the Bonner-Fischer behavior of the magnetic susceptibility. In the 2:1 ReO4- salt, two crystallographically independent organic slabs are interconnected through N-H ... O(Re) hydrogen bonds, demonstrating the overlooked hydrogen-bond acceptor capability of this anion. The salt exhibits metallic behavior with a weak localization below 200 K. Both structures reveal the occurrence of a strong C-H ... O hydrogen bond involving the aromatic CH group of the EDT-TTF core, which is activated by the neighboring amidic moiety. Together with the NH ... O hydrogen bond, it gives rise to a cyclic motif noted R-2(1)(7) in Etter's graph set analysis.
• Design and Evaluation of a Crystalline Hybrid of Molecular Conductors and Molecular Rotors
  作者：Cyprien Lemouchi、Cécile Mézière、Leokadiya Zorina、Sergey Simonov、Antonio Rodríguez-Fortea、Enric Canadell、Pawel Wzietek、Pascale Auban-Senzier、Claude Pasquier、Thierry Giamarchi、Miguel A. Garcia-Garibay、Patrick Batail

  DOI：10.1021/ja301484b

  日期：2012.5.9

  to 7.3 kcal mol(-1). Another is quantum dissipation, a phenomenon addressing the difference of dynamics of the rotors in the two solids with different electrical properties, by which the large number of degrees of freedom of the low dimensional electron gas may serve as a bath for the dissipation of the energy of the rotor motion, the two systems being coupled by the Coulomb interaction between the charges

  结合分子电导率和分子机械领域的最新概念，我们着手设计一种晶体分子导体，该导体也具有分子转子。我们报告了具有常见 1,4-双（羧乙炔基）双环 [2.2.2] 辛烷 (BABCO) 功能转子的两种固体的结构、电子和物理性质以及动力学。一种，[nBu(4)N(+)](2)[BABCO][BABCO(-)](2)，是一种无色绝缘体，其中二羧酸与其两种单阴离子共轭碱共结晶。另一种是通过电结晶自组装，呈黑色、闪亮的针状，具有 (EDT-TTF-CONH(2))(2)(+) (EDT-TTF = 乙撑二硫四硫富瓦烯) 和阴离子 [BABCO (-)] 转子。使用变温 (5-300 K) 质子自旋晶格弛豫，(1)HT(1)(-1)，我们能够在 [nBu(4)N(+)](2)[BABCO][BABCO(-)](2) 中分配两种类型的布朗旋转器。我们表明中性 BABCO 组在 300 K 时具有 120 GHz
• The crystal chemistry of amide‐functionalized ethylenedithiotetrathiafulvalenes: EDT‐TTF‐CONRR′ (R, R′ = H, Me)
  作者：Karine Heuzé、Marc Fourmigué、Patrick Batail

  DOI：10.1039/a902852h

  日期：——

  The preparation of ethylenedithiotetrathiafulvalenes (EDT-TTF) directly functionalized on the TTF core with a primary, secondary or tertiary amide or an hydrazide functional group is described. The X-ray crystal structures of EDT-TTF-CO 2 H, EDT-TTF-CONH 2 , EDT-TTF-CONHMe and EDT-TTF-CONMe 2 are reported. The solid state architectures adopted by those functionalized molecules appear to be a compromise between the hydrogen bond requirements of the OH, NH 2 , CH and CO groups, which act as hydrogen bond donor and acceptor, respectively, and the S···S van der Waals interactions of the EDT-TTF moiety. The activation of the hydrogen atom of the TTF core, ortho to the amidic group, enhances its involvement in short C–H···O bonds, giving rise to a characteristic chelating R 2 1 (7) motif as observed in the secondary amide, EDT-TTF-CONHMe.

  本文描述了在TTF核心上直接官能化的乙烯基二硫代四硫富瓦烯（EDT-TTF）的制备，该官能团具有伯、仲或叔酰胺或酰肼官能团。本文报道了EDT-TTF-CO2H、EDT-TTF-CONH2、EDT-TTF-CONHMe和EDT-TTF-CONMe2的X射线晶体结构。这些官能化分子采用的固态结构似乎是氢键要求之间的折衷，氢键分别由OH、NH2、CH和CO基团提供和接受，而EDT-TTF部分的S·S·S范德华相互作用。TTF核心氢原子的活化，邻位于酰胺基，增强了其参与短C-H·O键的能力，从而产生在仲酰胺EDT-TTF-CONHMe中观察到的特征螯合R2R1(7)结构。