5-(2-pyridyl)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione | 237401-51-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 5-(2-pyridyl)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione
• 英文别名: 4,5-(2-pyridylethylenedithio)-1,3-dithiole-2-thione；4,5-(2-pyridylethylene)-dithio-1,3-dithiol-2-thione；5-pyridin-2-yl-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-thione；1,3-Dithiolo[4,5-b][1,4]dithiin-2-thione, 5,6-dihydro-5-(2-pyridinyl)-；5-pyridin-2-yl-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione
• CAS: 237401-51-3
• 化学式: C₁₀H₇NS₅
• 分子量: 301.502
• InChiKey: XKQOZOYIRPBWPU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  146
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2-pyridyl)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione 在 mercury(II) diacetate 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以80%的产率得到4,5-(2-pyridylethylenedithio)-1,3-dithiol-2-one
  参考文献：
  名称：

  New electron donors: BEDT-TTF derivatives bearing a pyridine group; synthesis, crystal structure, electrochemical studies and the formation of charge transfer complexes

  摘要：

  合成了含有吡啶基的双（乙烯硫醚）四硫富瓦烯（BEDT-TTF）衍生物1a、b和2a、b，并通过循环伏安法研究了它们在二氯甲烷溶液中的氧化还原电位，结果表明它们的电子给体能力弱于BEDT-TTF。化合物2b通过X射线晶体学研究，揭示了其晶体格子的柱状包装模式。探讨了这些新给体与四氰基喹啉（TCNQ）、2,3-二氯-5,6-二氰基苯-1,4-醌（DDQ）及氯化铜（CuCl₂）形成的电荷转移（CT）复合物。其中，CT复合物1b•1.1·TCNQ和1a·CuCl₂在室温下显示出半导体范围内的导电性（1b•1.1·TCNQ的σ_rt = 1.6×10⁻³ S cm⁻¹，1a·CuCl₂的σ_rt = 4.3×10⁻³ S cm⁻¹，测量是在压缩后球粒上进行的）。根据X射线光电子能谱（XPS）和导电性测量的结果，我们建议复合物1a·CuCl₂中电荷转移和配位接触共存。

  DOI：

  10.1039/a900063a
• 作为产物：
  描述：

  2-乙烯基吡啶 、 1,3-dithiol-2,4,5-trithione 以 1,4-二氧六环 为溶剂， 反应 1.5h， 以20%的产率得到5-(2-pyridyl)-5,6-dihydro[1,3]dithiolo[4,5-b][1,4]dithiine-2-thione
  参考文献：
  名称：

  New electron donors: BEDT-TTF derivatives bearing a pyridine group; synthesis, crystal structure, electrochemical studies and the formation of charge transfer complexes

  摘要：

  合成了含有吡啶基的双（乙烯硫醚）四硫富瓦烯（BEDT-TTF）衍生物1a、b和2a、b，并通过循环伏安法研究了它们在二氯甲烷溶液中的氧化还原电位，结果表明它们的电子给体能力弱于BEDT-TTF。化合物2b通过X射线晶体学研究，揭示了其晶体格子的柱状包装模式。探讨了这些新给体与四氰基喹啉（TCNQ）、2,3-二氯-5,6-二氰基苯-1,4-醌（DDQ）及氯化铜（CuCl₂）形成的电荷转移（CT）复合物。其中，CT复合物1b•1.1·TCNQ和1a·CuCl₂在室温下显示出半导体范围内的导电性（1b•1.1·TCNQ的σ_rt = 1.6×10⁻³ S cm⁻¹，1a·CuCl₂的σ_rt = 4.3×10⁻³ S cm⁻¹，测量是在压缩后球粒上进行的）。根据X射线光电子能谱（XPS）和导电性测量的结果，我们建议复合物1a·CuCl₂中电荷转移和配位接触共存。

  DOI：

  10.1039/a900063a

文献信息

• Pyridyl-substituted [1,3]Dithiolo-[4,5-b][1,4]dithiine-2-thiones
  作者：A. Yu. Koshevaya、V. A. Starodub、D. Fenske

  DOI：10.1007/s10593-005-0157-9

  日期：2005.3
• Novel mercury(II) complexes of 1,3-dithiole-2-thiones containing the 2-pyridyl moiety: syntheses, X-ray crystal structures and solution behavior
  作者：Hye Jin Nam、Ha-Jin Lee、Dong-Youn Noh

  DOI：10.1016/j.poly.2003.09.028

  日期：2004.1

  The mercury(II) complexes of 5-pyridin-2-yl-5,6-dihydro-[1,3]dithiolo[4,5-b][1,4]dithiin-2-thione (2PyEDT-DTT: 1), [Hg(2PyEDT-DTT)X-2] (X=Cl (2a), Br (2b) and I (2c)) were obtained from the reaction of HgX2 and 2PyEDT-DTT. These complexes adopt a dimeric arrangement of [Hg(2PyEDT-DTT)X-2](2) through intermolecular Hg...N and Hg...S interactions. According to the FT-IR/UV-Vis/NMR spectroscopy data, these intermolecular interactions are cleaved in media containing trace H2O. [Hg(2PyDT-DTT)(2)] (3; 2PyDT-DTT: 5-(1-pyridin-2-yl-vinylsulfanyl)-2-thioxo-[1,3]dithiole-4-thiolate) was isolated from the filtrate of 2. The Hg(II) ion is located in a center of symmetry and adopts a distorted octahedral geometry with four sulfur atoms (two from the thiolate groups and two from the sulfide groups) and two nitrogen atoms from the pyridyl group. The time-dependent solution U-V-Vis and H-1 NMR measurements showed the transformation of 2PyDT-DTT to 2PyEDT-DTT caused by trace H2O in organic solvents. (C) 2003 Elsevier Ltd. All rights reserved.
• Synthesis and crystal structure of {(2-α-pyridylethyl)tris(phenyl)phosphonium}trichlorozinc(II)
  作者：V. A. Starodub、A. Yu. Stoesser

  DOI：10.1134/s1070328406110054

  日期：2006.11

  The structure of the complex (2-alpha-pyridylethyl)tris(phenyl)phosphonium}trichlorozinc(II), which is an unexpected product of the reaction of the Zn2+ ion with coordinated 4,5-(2-pyridylethylene)dithio-1, 3-dithiol-2-thione, is described. The reaction mechanism is studied by the ESI method of positive and negative ions. The crystals are monoclinic, space group P2(1)/c, a=16.129(3) angstrom, b=11.167(2) angstrom, c=14.874(3) angstrom, beta=91.77(3)degrees, Z=4. The Zn(II) atom has a quasi-tetrahedral environment of three chloride ions and one phosphonium cation coordinated at the nitrogen atom of the pyridyl fragment.
• Cobalt(II) and nickel(II) cloride complexes with 4,5-(n-pyridylethylene)-dithio-1,3-dithiol-2-thiones (n = 2, 4)
  作者：V. A. Starodub、A. Yu. Stoesser

  DOI：10.1134/s1070328407060085

  日期：2007.6

  The NiCl2 and CoCl2 complexes with 4,5-(2-pyridylethylene)-dithio-1,3-dithiol-2-thione (L-1) and 4,5-(4-pyridylethylene)-dithio-1,3-dithiol-2-thione (L-2) were described. The L-1 ligand shows bidentate coordination through the pyridyl N atoms and the thiol S atoms in a tetrahedral [CoCl2(L-1)] complex (I) and in an octahedral [NiCl2(L-1)2](MeCN)(2) complex (II). The L-2 ligand exhibits monodentate coordination through the pyridyl N atom in tetrahedral complexes [CoCl2(L-2)(2) (III) and [NiCl2(L-2)(2)] (IV). Complexes I, III, IV in crystal state are octahedral due to extra coordination of the thione S atoms or the chloride bridges responsible for the polymeric structure. The structure of the complex II center dot CH2Cl2 was determined by X-ray diffraction analysis. The crystals are monoclinic, space group P2(1)/c, a = 11.895(2) angstrom, b = 13.374(3) angstrom, c = 21.873(4) angstrom, beta = 95.30(3)degrees, Z = 2. The Ni atom has quasi-tetrahedral surrounding due to two chloride ions and two L-1 ligands coordinated through the pyridyl N atoms and the thiol S atoms.