| 1308251-19-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• CAS: 1308251-19-5
• 化学式: C₁₀H₇F₃N₃OS
• 分子量: 274.246
• InChiKey: ZGTVZDGVWFLBGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-(1-amino-2,2,2-trifluoroethylidene)-4-methoxybenzenecarboximidamide 在 盐酸 、 二氯化硫 、 三苯基锑 作用下， 以 乙醚 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Unsymmetrical 1λ³-1,2,4,6-Thiatriazinyls with Aryl and Trifluoromethyl Substituents: Synthesis, Crystal Structures, EPR Spectroscopy, and Voltammetry

  摘要：

  A general synthetic route to 3-trifluoromethyl-5-aryl-1 lambda(3)-1,2,4,6-thiatriazinyl radicals was developed. X-ray structures were obtained for all five neutral radicals and show that they exist in the solid state as cofacial dimers linked by S center dot center dot center dot S contacts. X-ray structures were also obtained for two of the precursor chlorothiatriazines along with several aryl N-imidoylamidines, p-methoxybenzamidine, and N-chlorosulfonyl-N,N'-benzamidine. Cyclic voltammetric studies were performed on the [R2C2N3S](center dot) radicals in CH3CN and CH2Cl2 with ["Bu4N][PF6] as the supporting electrolyte under vacuum conditions in an all-glass electrochemical cell. The results provide quasi-reversible formal potentials for the [R2C2N3S](-/0) process in the range of 0.61 to 0.47 V, irreversible peak potentials for the [R2C2N3S](0/+) process from 0.59 to 0.91 V at lower concentrations, and the appearance of a second, reversible oxidation process from 0.69 to 0.94 V at higher concentrations (versus the Fc(0/+). couple; Fc = ferrocene). This behavior was indicative of monomer dimer equilibrium in solution, as ascertained from digital models of the voltammograms. There is a small but measurable trend in both the oxidation and reduction potentials with varying remote aryl substituents. EPR spectra were obtained for all five neutral radicals in CH2Cl2 solutions, which confirm the concentration of the unpaired electron density on the heterocyclic core. Trends were also seen in the hyperfine splitting constants a(N) with varying remote aryl substituents. Calculations were performed for all three oxidation states of the [R2C2N3S](-/center dot/+) monomeric rings; the resulting theoretical redox energies correlate well with solution phase voltammetric data.

  DOI：

  10.1021/ic2003996

文献信息

• Unsymmetrical 1λ³-1,2,4,6-Thiatriazinyls with Aryl and Trifluoromethyl Substituents: Synthesis, Crystal Structures, EPR Spectroscopy, and Voltammetry
  作者：René T. Boeré、Tracey L. Roemmele、Xin Yu

  DOI：10.1021/ic2003996

  日期：2011.6.6

  A general synthetic route to 3-trifluoromethyl-5-aryl-1 lambda(3)-1,2,4,6-thiatriazinyl radicals was developed. X-ray structures were obtained for all five neutral radicals and show that they exist in the solid state as cofacial dimers linked by S center dot center dot center dot S contacts. X-ray structures were also obtained for two of the precursor chlorothiatriazines along with several aryl N-imidoylamidines, p-methoxybenzamidine, and N-chlorosulfonyl-N,N'-benzamidine. Cyclic voltammetric studies were performed on the [R2C2N3S](center dot) radicals in CH3CN and CH2Cl2 with ["Bu4N][PF6] as the supporting electrolyte under vacuum conditions in an all-glass electrochemical cell. The results provide quasi-reversible formal potentials for the [R2C2N3S](-/0) process in the range of 0.61 to 0.47 V, irreversible peak potentials for the [R2C2N3S](0/+) process from 0.59 to 0.91 V at lower concentrations, and the appearance of a second, reversible oxidation process from 0.69 to 0.94 V at higher concentrations (versus the Fc(0/+). couple; Fc = ferrocene). This behavior was indicative of monomer dimer equilibrium in solution, as ascertained from digital models of the voltammograms. There is a small but measurable trend in both the oxidation and reduction potentials with varying remote aryl substituents. EPR spectra were obtained for all five neutral radicals in CH2Cl2 solutions, which confirm the concentration of the unpaired electron density on the heterocyclic core. Trends were also seen in the hyperfine splitting constants a(N) with varying remote aryl substituents. Calculations were performed for all three oxidation states of the [R2C2N3S](-/center dot/+) monomeric rings; the resulting theoretical redox energies correlate well with solution phase voltammetric data.