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.