1,1,1-trifluoroacetone enolate radical | 64724-05-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氟化物
• 英文名称: 1,1,1-trifluoroacetone enolate radical
• 英文别名: 3,3,3-trifluoroacetonyl radical；(R)-2,2,2-trifluoro-1-methylethoxy
• CAS: 64724-05-6
• 化学式: C₃H₂F₃O
• 分子量: 111.043
• InChiKey: NWLPLONKXDSUGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1,1-三氟丙酮 在 过氧化苯甲酰 作用下， 以 1,1,2-三氯三氟乙烷（CFC-113） 为溶剂， 生成 1,1,1-trifluoroacetone enolate radical
  参考文献：
  名称：

  摘要：

  Absolute rate constants and some of their Arrhenius parameters were obtained by time-resolved electron spin resonance (ESR) spectroscopy for the addition of the 2-(alkoxycarbonyl)propan-2-yl and 3,3,3-trifluoroacetonyl (= 3,3,3-trifluoro-2-oxopropyl) radicals to a variety of mono- and 1,1-disubstituted alkenes. Their analysis shows that the addition of 2-(alkoxycarbonyl)propan-2-yl is mainly governed by the exothermicity of the reaction with slight modifications by nucleophilic and electrophilic effects giving rise to an overall ambiphilic behavior. In contrast, large electrophilic polar effects dominate the addition of the 3,3,3-trifluoroacetonyl (= 3,3,3-frifluoro-2-oxopropan-2-yl) radical, as it is expected from its large electron affinity. For both radicals, the activation energies are well-predicted by analytic equations for the enthalpic and polar terms. A comparison of the rate data of 2-(alkoxycarbonyl)propan-2-yl with the homo- and copolymerization rate constants of the propagating radical of methyl methacrylate shows that the additions of these structurally related low- and high-molecular-weight radicals to alkenes are governed by very similar effects.

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<658::aid-hlca658>3.0.co;2-z

文献信息

• ——
  作者：Torsten Zytowski、Bernhard Knühl、Hanns Fischer

  DOI：10.1002/(sici)1522-2675(20000315)83:3<658::aid-hlca658>3.0.co;2-z

  日期：2000.3.15

  Absolute rate constants and some of their Arrhenius parameters were obtained by time-resolved electron spin resonance (ESR) spectroscopy for the addition of the 2-(alkoxycarbonyl)propan-2-yl and 3,3,3-trifluoroacetonyl (= 3,3,3-trifluoro-2-oxopropyl) radicals to a variety of mono- and 1,1-disubstituted alkenes. Their analysis shows that the addition of 2-(alkoxycarbonyl)propan-2-yl is mainly governed by the exothermicity of the reaction with slight modifications by nucleophilic and electrophilic effects giving rise to an overall ambiphilic behavior. In contrast, large electrophilic polar effects dominate the addition of the 3,3,3-trifluoroacetonyl (= 3,3,3-frifluoro-2-oxopropan-2-yl) radical, as it is expected from its large electron affinity. For both radicals, the activation energies are well-predicted by analytic equations for the enthalpic and polar terms. A comparison of the rate data of 2-(alkoxycarbonyl)propan-2-yl with the homo- and copolymerization rate constants of the propagating radical of methyl methacrylate shows that the additions of these structurally related low- and high-molecular-weight radicals to alkenes are governed by very similar effects.