3,3′-[(3-ethyl-2-oxo-2,3-dihydro-1,3-thiazole-4,5-diyl)bis(seleno)]dipropanenitrile | 1402606-66-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,3′-[(3-ethyl-2-oxo-2,3-dihydro-1,3-thiazole-4,5-diyl)bis(seleno)]dipropanenitrile
• CAS: 1402606-66-9
• 化学式: C₁₁H₁₃N₃OSSe₂
• 分子量: 393.23
• InChiKey: HGXJWPJJZJHJLE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.25
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  69.58
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,3′-[(3-ethyl-2-oxo-2,3-dihydro-1,3-thiazole-4,5-diyl)bis(seleno)]dipropanenitrile 、 四苯基氯化膦 在 sodium methylate 、 potassium tetrachloroaurate(III) 作用下， 以 甲醇 为溶剂， 反应 4.5h， 以27%的产率得到
  参考文献：
  名称：

  Anisotropic Chemical Pressure Effects in Single-Component Molecular Metals Based on Radical Dithiolene and Diselenolene Gold Complexes

  摘要：

  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.

  DOI：

  10.1021/ja3065649
• 作为产物：
  描述：

  3-Ethyl-2-methylsulfanyl-thiazol-3-ium; iodide 在 sodium methylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 6.0h， 生成 3,3′-[(3-ethyl-2-oxo-2,3-dihydro-1,3-thiazole-4,5-diyl)bis(seleno)]dipropanenitrile
  参考文献：
  名称：

  Anisotropic Chemical Pressure Effects in Single-Component Molecular Metals Based on Radical Dithiolene and Diselenolene Gold Complexes

  摘要：

  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.

  DOI：

  10.1021/ja3065649