N-(2,4,6-trinitrophenyl)-2,2,2-trifluoroethylamine | 31577-23-8

• 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: N-(2,4,6-trinitrophenyl)-2,2,2-trifluoroethylamine
• 英文别名: 2,4,6-trinitro-N-(2,2,2-trifluoroethyl)aniline
• CAS: 31577-23-8
• 化学式: C₈H₅F₃N₄O₆
• 分子量: 310.146
• InChiKey: ZMOFILCPEHMWGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  150
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,4,6-三硝基氯苯 、 2,2,2-三氟乙基胺 以 水 为溶剂， 生成 N-(2,4,6-trinitrophenyl)-2,2,2-trifluoroethylamine
  参考文献：
  名称：

  Nucleophilic reactivity: nucleophilic aromatic substitution reactions of 2,4-dinitrochlorobenzene and picryl chloride in aqueous and methanol solutions

  摘要：

  Rate constants for nucleophilic aromatic substitution reactions of picryl chloride, I, with acetate ion and a series of amine nucleophiles, including primary, secondary, tertiary (quinuclidines), and amines which show the alpha-effect, in aqueous and methanol solutions have been measured. Rate constants have also been measured, in water, for the reactions of 2,4-dinitrochlorobenzene, II, with trifluoroethylamine and semicarbazide. Reactions of picryl chloride with 3-quinuclidinol and DABCO yield picrate ion via general base catalyzed hydrolysis. On the other hand, reaction with quinuclidine proceeds at least in part via a mechanism in which N-picrylquinuclidinium ion is formed and then converted into a N-picrylpiperidine derivative. When the kinetic data are combined with data previously reported in the literature, the slopes of plots of log of the second-order rate constants against Ritchie's N+ parameter are 0.95 +/- 0.13 and 0.79 +/- 0.11 for the reactions of 2,4-dinitrochlorobenzene and picryl chloride, respectively (the reported error limits are the 95% confidence intervals). Steric effects may be important in these reactions, but these effects do not significantly change the slopes of the N+ correlation lines. The slope smaller than one for the reactions of picryl chloride is consistent with decreased selectivity towards nucleophilic attack, and with the modified form of Ritchie's equation, log k = S+N+ + log k0, in which relative nucleophilic reactivities are substrate dependent.

  DOI：

  10.1021/jo00041a021