1-methyl-3-(2-hydroxyiminopropyl)imidazolium bromide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-methyl-3-(2-hydroxyiminopropyl)imidazolium bromide
• 英文别名: 1-Methyl-3-(2-hydroxyiminopropyl)imidazolium bromide；N-[1-(3-methylimidazol-3-ium-1-yl)propan-2-ylidene]hydroxylamine;bromide
• 化学式: Br*C₇H₁₂N₃O
• 分子量: 234.096
• InChiKey: ZYYIUROCAFSVPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.83
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  对硫磷(乙基对硫磷) 、 1-methyl-3-(2-hydroxyiminopropyl)imidazolium bromide 以 水 为溶剂， 生成 4-硝基苯酚阴离子 、
  参考文献：
  名称：

  功能化表面活性剂1-十六烷基-3-（2-羟基亚氨基丙基）咪唑鎓卤化物与对硝基苯基对甲苯磺酸酯，对硝基苯基磷酸二乙酯和对硝基苯基乙基膦酸酯的胶束效应

  摘要：

  1-Cetyl-3-(2-hydroxyiminopropyl)imidazolium chloride and bromide were synthesized for the first time. These compounds are functionalized zwitterionic surfactants which give rise to micelle formation in aqueous solution. Kinetic and thermodynamic analysis of nucleophilic cleavage of p-nitrophenyl p-toluenesulfonate, diethyl p-nitrophenyl phosphate, and ethyl p-nitrophenyl ethylphosphonate in the presence of 1-cetyl-3-(2-hydroxyiminopropyl)irriidazolium halide micelles showed that the latter are powerful nucleophilic reagents whose kinetic behavior can be described in terms of a simple pseudophase distribution model. The efficiency of substrate solubilization with zwitterionic surfactant micelles and the reactivity of the oximate fragment in the micelle phase were estimated on a quantitative level. The observed acceleration of S(N)2 reactions with the examined p-nitrophenyl esters relative to analogous reactions of zwitterionic 1-methyl-3-(2-hydroxyiniinopropyl)imidazolium halides is, respectively, 12800, 550, and 900 times; it is explained mainly by increased concentration of the reactants in micelles.

  DOI：

  10.1023/a:1021655813700
• 作为产物：
  描述：

  3-Methyl-1-(2-oxo-propyl)-3H-imidazol-1-ium; bromide 在 羟胺 作用下， 以 甲醇 为溶剂， 生成 1-methyl-3-(2-hydroxyiminopropyl)imidazolium bromide
  参考文献：
  名称：

  功能化表面活性剂1-十六烷基-3-（2-羟基亚氨基丙基）咪唑鎓卤化物与对硝基苯基对甲苯磺酸酯，对硝基苯基磷酸二乙酯和对硝基苯基乙基膦酸酯的胶束效应

  摘要：

  1-Cetyl-3-(2-hydroxyiminopropyl)imidazolium chloride and bromide were synthesized for the first time. These compounds are functionalized zwitterionic surfactants which give rise to micelle formation in aqueous solution. Kinetic and thermodynamic analysis of nucleophilic cleavage of p-nitrophenyl p-toluenesulfonate, diethyl p-nitrophenyl phosphate, and ethyl p-nitrophenyl ethylphosphonate in the presence of 1-cetyl-3-(2-hydroxyiminopropyl)irriidazolium halide micelles showed that the latter are powerful nucleophilic reagents whose kinetic behavior can be described in terms of a simple pseudophase distribution model. The efficiency of substrate solubilization with zwitterionic surfactant micelles and the reactivity of the oximate fragment in the micelle phase were estimated on a quantitative level. The observed acceleration of S(N)2 reactions with the examined p-nitrophenyl esters relative to analogous reactions of zwitterionic 1-methyl-3-(2-hydroxyiniinopropyl)imidazolium halides is, respectively, 12800, 550, and 900 times; it is explained mainly by increased concentration of the reactants in micelles.

  DOI：

  10.1023/a:1021655813700

文献信息

• ——
  作者：Yu. S. Simanenko、A. F. Popov、E. A. Karpichev、T. M. Prokop'eva、V. A. Savelova、C. A. Bunton

  DOI：10.1023/a:1021655813700

  日期：——

  1-Cetyl-3-(2-hydroxyiminopropyl)imidazolium chloride and bromide were synthesized for the first time. These compounds are functionalized zwitterionic surfactants which give rise to micelle formation in aqueous solution. Kinetic and thermodynamic analysis of nucleophilic cleavage of p-nitrophenyl p-toluenesulfonate, diethyl p-nitrophenyl phosphate, and ethyl p-nitrophenyl ethylphosphonate in the presence of 1-cetyl-3-(2-hydroxyiminopropyl)irriidazolium halide micelles showed that the latter are powerful nucleophilic reagents whose kinetic behavior can be described in terms of a simple pseudophase distribution model. The efficiency of substrate solubilization with zwitterionic surfactant micelles and the reactivity of the oximate fragment in the micelle phase were estimated on a quantitative level. The observed acceleration of S(N)2 reactions with the examined p-nitrophenyl esters relative to analogous reactions of zwitterionic 1-methyl-3-(2-hydroxyiniinopropyl)imidazolium halides is, respectively, 12800, 550, and 900 times; it is explained mainly by increased concentration of the reactants in micelles.