N-ethyl-1,3-thiazoline 2-thione | 33120-64-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-ethyl-1,3-thiazoline 2-thione
• 英文别名: 3-Ethyl-1,3-thiazole-2-thione
• CAS: 33120-64-8
• 化学式: C₅H₇NS₂
• 分子量: 145.249
• InChiKey: MNNQROJSTCCACI-UHFFFAOYSA-N

物化性质

• 沸点：
  210.9±23.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-ethyl-1,3-thiazoline 2-thione 在 正丁基锂 、 全氟己基碘烷 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 以65%的产率得到3-ethyl-5-iodothiazole-2(3H)-thione
  参考文献：
  名称：

  结晶碘代二硫代-2-硫酮和噻唑-2-硫酮中的 C S⋯I卤素键相互作用†

  摘要：

  以二卤化物（I 2，IBr或ICl）作为XB供体已经很好地确立了硫酮中sp 2硫原子充当卤素键（XB）受体的倾向，但有机XB供体却很少进行研究。四个碘化杂环的晶体结构，即1，3-二硫代-2-硫酮和N-乙基噻唑-2-硫酮的单和二碘代衍生物，为评估这种C–I⋯的强度和方向性提供了机会。 S互动。我们在这里描述了3-乙基-5-碘噻唑-2（3 H）-硫酮和3-乙基-4,5-二碘噻唑-2（3 H）-硫酮的原始合成以及这四种化合物的固态结构，特别注意卤素键（C–I⋯SC）和氢键（C–H⋯I，S）发生在晶体中，这与四个分子的计算出的静电表面电势（ESP）的特殊性有关。噻唑-2-硫酮中的硫酮硫原子表现出比二硫醇-2-硫酮中更好的XB受体，并且电荷浓度区域发生了明显的变形。单碘化衍生物4-碘-1,3-二硫代-2-硫酮和3-乙基-5-碘噻唑-2-硫酮的特征是氢原子的静电表面电势的极值可与氢原子相比。相邻的碘原

  DOI：

  10.1039/c6ce00822d
• 作为产物：
  描述：

  [NEt₄][Zn(Et-thiazds)₂] 在 盐酸 作用下， 以 二氯甲烷 为溶剂， 生成 N-ethyl-1,3-thiazoline 2-thione
  参考文献：
  名称：

  Diselenolene proligands: reactivity and comparison with their dithiolene congeners

  摘要：

  噻吩和二噻吩是从二噻吩前体合成的。

  DOI：

  10.1039/d1nj01335a

文献信息

• Efficient routes towards a series of 5,5′-bithiazolidinylidenes as π-electron acceptors
  作者：Y. Le Gal、D. Ameline、N. Bellec、A. Vacher、T. Roisnel、V. Dorcet、O. Jeannin、D. Lorcy

  DOI：10.1039/c5ob01169h

  日期：——

  Among different approaches, the thermal treatment of the fused bicycle involving a dithiole-2-one ring is the most efficient one and opens access to a variety of π-conjugated electron acceptors.

  在众多方法中，涉及二硫杂环-2-酮环的融合自行车的热处理是最有效的方法，它为多种π-共轭电子受体提供了途径。
• Radical or Not Radical: Compared Structures of Metal (M = Ni, Au) Bis-Dithiolene Complexes with a Thiazole Backbone
  作者：Agathe Filatre-Furcate、Nathalie Bellec、Olivier Jeannin、Pascale Auban-Senzier、Marc Fourmigué、Antoine Vacher、Dominique Lorcy

  DOI：10.1021/ic501293z

  日期：2014.8.18

  diffraction. The paramagnetic anionic complex [Ni(Et-thiazdt)2]−1, as Ph4P+ salt, exhibits side-by-side lateral interactions leading to a Heisenberg spin chain behavior. The solid-state structure of the neutral, diamagnetic [Ni(Et-thiazdt)2]0 complex shows a face-to-face organization with a large longitudinal shift, at variance with the structure of its radical and neutral gold dithiolene analogue described

  配制成[Ni（Et-thiazdt）2 ] n，n = -2，-1、0和Et-thiazdt的完整系列的双阴离子，单阴离子和中性二硫代噻吩配合物：N-乙基-1,3-噻唑啉-2-硫酮-4,5-二硫代磺酸盐是使用前面所述的针对N-Me衍生物的优化程序制备的。电化学和光谱性质证实了Eth-thiazdt dithiolate配体的富电子特征。通过单晶X射线衍射在结构上表征这三种配合物。顺磁性阴离子络合物[Ni（Et-thiazdt）2 ] -1，为Ph 4 P +盐，表现出并排的横向相互作用，导致海森堡自旋链行为。中性，抗磁性的[Ni（Et-thiazdt）2 ] 0配合物的固态结构显示出具有较大纵向位移的面对面组织，与其先前所述的其自由基和中性二硫代金类似物的结构不同并表述为[Au（Et-thiazdt）2 ] •。Ni / Au二硫代亚硒酸盐络合物的两个结构以及其他少数结构特征对的结构的比较
• A Single-Component Molecular Metal Based on a Thiazole Dithiolate Gold Complex
  作者：Nadine Tenn、Nathalie Bellec、Olivier Jeannin、Lidia Piekara-Sady、Pascale Auban-Senzier、Jorge Íñiguez、Enric Canadell、Dominique Lorcy

  DOI：10.1021/ja907426s

  日期：2009.11.25

  reaching 1000 S x cm(-1) at 21 kbar. At 13 kbar there is a crossover between semiconducting and metallic regimes. Thus, the present system is the first well characterized single-component molecular metal without TTF dithiolate ligands. First-principles DFT calculations show that the ground state is antiferromagnetic with a very small band gap. A simulation of the effect of pressure on the electronic structure

  单组分分子导体已从基于 N-乙基-1,3-噻唑啉-2-硫酮-4,5-二硫醇 (Et-thiazdt) 配体的单阴离子金双 (dithiolene) 配合物的电结晶中分离出来。该系统的晶体结构展示了由平面分子的平行均匀一维堆叠构建的层。在室温和环境压力下，该系统是半导体 (0.33 S x cm(-1))，具有很小的活化能。然而，单晶电导率是强烈的压力依赖达到 1000 S x cm(-1) 在 21 kbar。在 13 kbar 时，半导体和金属状态之间存在交叉。因此，本系统是第一个没有TTF二硫醇配体的充分表征的单组分分子金属。第一性原理 DFT 计算表明基态是反铁磁性的，带隙非常小。压力对电子结构影响的模拟为观察到的电导率变化提供了基本原理，并提供了有关如何进一步稳定系统金属状态的见解。
• Anisotropic Chemical Pressure Effects in Single-Component Molecular Metals Based on Radical Dithiolene and Diselenolene Gold Complexes
  作者：Gilles Yzambart、Nathalie Bellec、Ghassan Nasser、Olivier Jeannin、Thierry Roisnel、Marc Fourmigué、Pascale Auban-Senzier、Jorge Íñiguez、Enric Canadell、Dominique Lorcy

  DOI：10.1021/ja3065649

  日期：2012.10.17

  On the basis of the reported radical neutral complex [Au(Et-thiazdt)(2)] (Et-thiazdt = N-ethyl-1,3-thiazoline-2-thione-4,5-dithiolate), a series of single-component conductors derived from [Au(Et-thiazdt)(2)], also noted as [AuS4(=S)(2)], has been developed, by replacing the outer sulfur atoms of the thiazoline-2-thione rings by oxygen atoms and/or by replacing the coordinating sulfur atoms by selenium atoms toward the corresponding diselenolene complexes. Comparison of the X-ray crystal structures and transport properties of the four isostructural complexes, noted as [AuS4(=S)(2)], [AuS4(=O)(2)], [AuSe4(=S)(2)], and [AuSe4(=O)(2)], shows that the oxygen substitution on the outer thiazoline ring actually decreases the conductivity by a factor of 100, despite a contracted unit cell volume reflecting a positive chemical pressure effect. On the other hand, the S/Se substitution increases the conductivity by a factor of 100, and the pressure needed to transform these semiconductors into the metallic state is shifted from 13 kbar in [AuS4(=S)(2)] to only approximate to 6 kbar in [AuSe4(=S)(2)] Analysis of unit cell evolutions and ab initio band structure calculations demonstrates the strongly anisotropic nature of this chemical pressure effect and provides an explanation for the observed changes in conductivity. The greater sensitivity of these neutral single-component conductors to external pressure, as compared with "classical" radical salts, is also highlighted.
• Structure–Property Relationships in Pt ^II Diimine‐Dithiolate Nonlinear Optical Chromophores Based on Arylethylene‐1,2‐dithiolate and 2‐Thioxothiazoline‐4,5‐dithiolate
  作者：Anna Pintus、M. Carla Aragoni、Nathalie Bellec、Francesco A. Devillanova、Dominique Lorcy、Francesco Isaia、Vito Lippolis、Rebecca A. M. Randall、Thierry Roisnel、Alexandra M. Z. Slawin、J. Derek Woollins、Massimiliano Arca

  DOI：10.1002/ejic.201200346

  日期：2012.8

  AbstractEighteen new [PtII(N∧N)(S∧S)] complexes [23–40; N∧N = diimine: 2,2′‐bipyridine, 1,10‐phenanthroline and alkyl/aryl‐substituted derivatives; S∧S = arylethylene‐1,2‐dithiolate (R‐edt2–: R = phenyl, 2‐naphthyl, 1‐pyrenyl), N‐substituted 2‐thioxothiazoline‐4,5‐dithiolate (R‐dmet2–: R = methyl, ethyl, phenyl)] have been synthesized and characterized by spectroscopic (UV/Vis/NIR, fluorescence) and electrochemical (CV) measurements. Single‐crystal X‐ray diffraction analysis allowed structural characterization of five of the complexes (27–29, 31, and 37). Structural modifications capable of affecting the nature and energies of the frontier molecular orbitals in these systems were assessed and hybrid DFT and time‐dependent (TD) DFT calculations, carried out both in the gas phase and in the presence of several solvents (CH2Cl2, CHCl3, CH3CN, acetone, thf, dmf, dmso, and toluene), allowed the trends observed in the voltammetric data and in the energies of the peculiar solvatochromic visible absorption bands to be rationalized. In addition, to evaluate the second‐order nonlinear optical properties of 23–40, first static hyperpolarizability values βtot were calculated both in the gas phase and in CH2Cl2, the highest values being obtained for [Pt(N∧N)(Me‐dmet)] complexes (N∧N = 4,4′‐diphenyl‐2,2′‐bipyridine and 4,7‐diphenyl‐1,10‐phenanthroline; βtot = 691 × 10–30 and 604 × 10–30 esu, respectively).