1-(4-(Trifluoromethyl)phenyl)ethenone | 68998-27-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮
• 英文名称: 1-(4-(Trifluoromethyl)phenyl)ethenone
• CAS: 68998-27-6
• 化学式: C₉H₆F₃O
• 分子量: 187.141
• InChiKey: AAHLVJULVKHCLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-phenoxy-1-(4-(trifluoromethyl)phenyl)ethan-1-one 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-(4-(Trifluoromethyl)phenyl)ethenone
  参考文献：
  名称：

  Electrochemistry of Electron Transfer Probes. Observation of the Transition from Activation to Counterdiffusion Control in the Fragmentation of α-Aryloxyacetophenone Radical Anions^1a

  摘要：

  The cleavage of radical anions of substituted alpha-phenoxyacetophenones, X-C6H4COCH2OPh, IIa-k, has been studied in DMF by voltammetric and coulometric techniques. The standard potentials (E degrees) for formation of and rate constants, k, for the cleavage of the radical anions were determined using linear sweep voltammetry, LSV, together with digital simulation and previously reported laser flash photolysis data. The rate constants cover a range of almost eight orders of magnitude (0.4 s(-1) for X = p-MeCO- to 1.3.10(7) s(-1) for X = p-MeO-). The relative driving forces, Delta Delta G degrees(het)(RX.-), for the heterolytic cleavage of the radical anions (to give R-. + X-) were estimated from thermochemical cycles. A combined plot of log(k) versus Delta Delta G(het)degrees(RX.-) for the radical anions of IIa-k and of alpha-aryloxyacetophenones gave a curve with alpha = 0.5 at high driving forces and alpha = 1 at low driving forces, where alpha = partial derivative Delta G(0)(double dagger)/partial derivative Delta G degrees. The plot was analyzed using a model in which reversible cleavage of the radical anions takes place inside the solvent cage followed by (counter)diffusion of the fragments out of the solvent cage. The change in the value of a is interpreted as a change in the rate limiting process from chemical activation (i.e.,, fragmentation) to counterdiffusion. The model allowed the determination of the absolute values of Delta G(het)degrees(RX.-) and the intrinsic barrier, Delta G(0)(double dagger), for the fragmentation of the radical anions (8 +/- 1 kcal mol(-1), 0.35 eV). This leads to an estimate of the homolytic bond dissociation free energy of the C-OPh bond in the unsubstituted alpha-phenoxyacetophenone.

  DOI：

  10.1021/ja963374u