4,4'-Dinitrophenyl-d8-disulfide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4'-Dinitrophenyl-d8-disulfide
• 英文别名: 1,2,4,5-Tetradeuterio-3-nitro-6-[(2,3,5,6-tetradeuterio-4-nitrophenyl)disulfanyl]benzene
• 化学式: C₁₂H₈N₂O₄S₂
• 分子量: 316.275
• InChiKey: KWGZRLZJBLEVFZ-PGRXLJNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  氯苯-D5 在 sodium sulfide 、 sodium hydroxide 、 氘代硫酸 、 硝酸-d 作用下， 以 乙醇 、 重水 为溶剂， 反应 7.0h， 生成 4,4'-Dinitrophenyl-d8-disulfide
  参考文献：
  名称：

  Generation, Isolation, and Characterization of N-(Arylthio)-7-tert-butyl- and N-(Arylthio)-2,7-di-tert-butyl-1-pyrenylaminyl Radicals

  摘要：

  N-(Arylthio)-7-tert-butyl-1-pyrenylaminyl (2) and N-[(4-nitrophenyl)thio]-2,7-di-tert-butyl-1-pyrenylaminyl radicals (3) are prepared by PbO2 oxidation of N-(arylthio)-7-tert-butyl-1-aminopyrenes and N-[(4-nitrophenyl)thio] -2,7-di-tert-butyl-1-aminopyrene, respectively, and studied by ESR and ENDOR spectroscopy. The kinetic ESR study shows that, while aminyls 2 gradually decompose in solution at room temperature, aminyl 3 is quite persistent, even in refluxing benzene, and shows no tendency to dimerize, even at low temperatures. These interesting properties of 3 permit us to isolate 3 as radical crystals in 28-31% yield. The hyperfine splitting (hfs) constants of 2 and 3, determined by ESR and ENDOR spectroscopic methods, show an extensive delocalization of the unpaired electron onto the pyrene ring. Comparison of the hfs constants of 2 and 3 shows that a more extensive delocalization of the spin into the pyrene ring takes place in 3. This is accounted for in terms of the difference in the conformations of 2 and 3.

  DOI：

  10.1021/jo00091a015

文献信息

• Generation, Isolation, and Characterization of N-(Arylthio)-7-tert-butyl- and N-(Arylthio)-2,7-di-tert-butyl-1-pyrenylaminyl Radicals
  作者：Yozo Miura、Eiji Yamano、Akio Tanaka、Jun Yamauchi

  DOI：10.1021/jo00091a015

  日期：1994.6

  N-(Arylthio)-7-tert-butyl-1-pyrenylaminyl (2) and N-[(4-nitrophenyl)thio]-2,7-di-tert-butyl-1-pyrenylaminyl radicals (3) are prepared by PbO2 oxidation of N-(arylthio)-7-tert-butyl-1-aminopyrenes and N-[(4-nitrophenyl)thio] -2,7-di-tert-butyl-1-aminopyrene, respectively, and studied by ESR and ENDOR spectroscopy. The kinetic ESR study shows that, while aminyls 2 gradually decompose in solution at room temperature, aminyl 3 is quite persistent, even in refluxing benzene, and shows no tendency to dimerize, even at low temperatures. These interesting properties of 3 permit us to isolate 3 as radical crystals in 28-31% yield. The hyperfine splitting (hfs) constants of 2 and 3, determined by ESR and ENDOR spectroscopic methods, show an extensive delocalization of the unpaired electron onto the pyrene ring. Comparison of the hfs constants of 2 and 3 shows that a more extensive delocalization of the spin into the pyrene ring takes place in 3. This is accounted for in terms of the difference in the conformations of 2 and 3.