4-(三氟甲基)-1,2-二硫杂-3,5lambda2-二氮杂环戊-3-烯 | 118436-71-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂环化合物
• 中文名称: 4-(三氟甲基)-1,2-二硫杂-3,5lambda2-二氮杂环戊-3-烯
• 英文名称: 4-(Trifluormethy)-1,2,3,5-dithiadiazol
• 英文别名: 4-Trifluormethyl-1,2-dithia-3,5-diazolradikal；4-Trifluoromethyl-1,2,3,5-dithiadiazolyl；1,2,3,5-Dithiadiazolyl radical, 4-(trifluoromethyl)-
• CAS: 118436-71-8
• 化学式: C₂F₃N₂S₂
• 分子量: 173.163
• InChiKey: FIAFKJZFTCIKSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-(Trifluormethyl)-1,2,3,5-dithiadiazolium-chlorid 在 铜 、 锌 作用下， 以 liquid sulphur dioxide 为溶剂， 反应 18.0h， 以39%的产率得到4-(三氟甲基)-1,2-二硫杂-3,5lambda2-二氮杂环戊-3-烯
  参考文献：
  名称：

  EPR STUDIES OF THE BISTABILITY IN CF₃CNSSN

  摘要：

  Condensation of CF3C(=NH)NH2 With SCl2 yielded the dithiadiazolylium salt, [CF3CNSSN]Cl which could be reduced to[CF3CNSSN](2) with Zn/Cu couple in SO2. [CF3CNSSN](2) is a diamagnetic dimer in the solid state but melts at 308 K to give a paramagnetic liquid. On cooling the radical enters a metastable state before immediately resolidifying below 295 K The thermal hysteresis was probed by EPR spectroscopy. Metastable samples spontaneously solidified after an induction period, typically between ca. 5 and 30 min, consistent with the variable time necessary to form a seed crystal from which crystallization can occur

  DOI：

  10.1080/10426500490427637

文献信息

• The preparation and isolation of 5-methyl-1,3,2,4-dithiadiazolyl and the facile rearrangement of the 1,3,2,4-dithiadiazolyl radicals to the disulphide isomers, 2,3,1,4-dithiadiazolyl
  作者：Neil Burford、Jack Passmore、Melbourne J. Schriver

  DOI：10.1039/c39860000140

  日期：——

  The radical 5-methyl-1,3,2,4-dithiadiazolyl has been prepared and isolated, and it and two new derivatives undergo essentially quantitative isomerisation to 2,3,1,4-dithiadiazolyl at room temperature; the rate of isomerisation follows second order kinetics and the mechanism is postulated to involve an unstable π*–π* dimer intermediate.

  已经制备并分离了5-甲基-1,3,2,4-二噻二唑基，它和两个新的衍生物在室温下基本上定量地异构化为2,3,1,4-二噻二唑基。异构化速率遵循二阶动力学，并且推测该机理涉及不稳定的π* –π *二聚体中间体。
• Electron spin resonance spectroscopy of free radicals
  作者：Shirley A. Fairhurst、Leslie H. Sutcliffe、Keith F. Preston、Arthur J. Banister、Andrew S. Partington、Jeremy M. Rawson、Jack Passmore、Melbourne J. Schriver

  DOI：10.1002/mrc.1260311114

  日期：1993.11

  powder ESR spectra of the 4‐trifluoromethyl‐1,2,3,5‐dithiadiazolyl and 4‐pentafluorophenyl‐1,2,3,5‐dithiadiazolyl free radicals were analysed. Comparison of the ESR parameters with those obtained for the protonated equivalents shows that fluorination produces a drift of unpaired electron spin density away from the nitrogen 2px orbitals towards sulphur 3px orbitals (x is the direction perpendicular to the

  分析了 4-三氟甲基-1,2,3,5-二噻二唑基和 4-五氟苯基-1,2,3,5-二噻二唑基自由基的溶液和粉末 ESR 光谱。将 ESR 参数与质子化等效物获得的参数进行比较表明，氟化产生了未配对电子自旋密度从氮 2px 轨道向硫 3px 轨道（x 是垂直于杂环的方向）的漂移，与取代基的电负性。氟化自由基比质子化自由基更容易二聚化。
• Thermal hysteresis in dithiadiazolyl and dithiazolyl radicals induced by supercooling of paramagnetic liquids close to room temperature: a study of F₃CCNSSN and an interpretation of the behaviour of F₃CCSNSCCF₃
  作者：Hongbin Du、Robert C. Haddon、Ingo Krossing、Jack Passmore、Jeremy M. Rawson、Melbourne J. Schriver

  DOI：10.1039/b202627a

  日期：——

  The trifluoromethyl-substituted dithiadiazolyl and dithiazolyl radicals, F3CCNSSN (1) and F3CCSNSCCF3 (2) associate through π*–π* covalent and electrostatic Sδ+…Nδ− interactions in the solid state, but melt with a dramatic volume increase to generate paramagnetic liquids; these radicals exhibit thermal hysteresis, which arises through a meta-stable super-cooled liquid state, close to room temperature.

  三氟甲基取代的二噻二唑基和二噻唑基 F3CCNSSN (1) 和 F3CCSNSCCF3 (2) 在固态下通过 π*-π* 共价和静电 Sδ+...Nδ- 相互作用结合在一起，但随着体积急剧增大而熔化，生成顺磁性液体；这些自由基表现出热滞后，通过接近室温的元稳定超冷液态而产生。
• Hoefs, Hans-Ulrich; Bats, Jan W.; Gleiter, Rolf, Chemische Berichte, 1985, vol. 118, # 9, p. 3781 - 3804
  作者：Hoefs, Hans-Ulrich、Bats, Jan W.、Gleiter, Rolf、Hartmann, Gabriele、Mews, Ruediger et al.

  DOI：——

  日期：——
• Hoefs, Hans-Ulrich; Hartmann, Gabriele; Mews, Ruediger, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1984, vol. 39, # 10, p. 1389 - 1392
  作者：Hoefs, Hans-Ulrich、Hartmann, Gabriele、Mews, Ruediger、Sheldrick, George M.

  DOI：——

  日期：——