4-(Trifluoromethyl)phenoxyradical | 73073-68-4

• 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-(Trifluoromethyl)phenoxyradical
• CAS: 73073-68-4
• 化学式: C₇H₄F₃O
• 分子量: 161.103
• InChiKey: RVTBFVQHBHDXMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 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：

  对三氟甲基苯酚 在 (1-溴-2-甲基丙烷-2-基)苯 、 六正丁基二锡 作用下， 以 苯 为溶剂， 生成 4-(Trifluoromethyl)phenoxyradical
  参考文献：
  名称：

  取代酚对烷基自由基的反应性

  摘要：

  伯烷基自由基与取代酚类化合物反应的速率常数已在室温下在苯或甲苯中使用自由基时钟技术测量。使用三种具有代表性的苯酚，在邻位含有不同大小的取代基，在不同温度下研究了氢转移到烷基的动力学以获得相应的阿伦尼乌斯参数。还在作为氢键受体的六种不同溶剂中研究了动力学溶剂对与 α-生育酚反应的影响，同时研究了与 2,4,6-三甲基苯酚和 2,6-二叔丁基苯酚在甲苯和γ-戊内酯。对于某些酚类，还研究了自聚集对动力学参数的影响。

  DOI：

  10.1021/ja982405d

文献信息

• Reactivity of Substituted Phenols Toward Alkyl Radicals
  作者：Paola Franchi、Marco Lucarini、Gian Franco Pedulli、Luca Valgimigli、Bruno Lunelli

  DOI：10.1021/ja982405d

  日期：1999.1.1

  The rate constants for the reaction of primary alkyl radicals with substituted phenolic compounds have been measured in benzene or toluene at room temperature by using the radical clock technique. With three representative phenols, containing in the ortho positions substituents of different size, the kinetics of the hydrogen transfer to alkyl radicals was studied at different temperatures to obtain the

  伯烷基自由基与取代酚类化合物反应的速率常数已在室温下在苯或甲苯中使用自由基时钟技术测量。使用三种具有代表性的苯酚，在邻位含有不同大小的取代基，在不同温度下研究了氢转移到烷基的动力学以获得相应的阿伦尼乌斯参数。还在作为氢键受体的六种不同溶剂中研究了动力学溶剂对与 α-生育酚反应的影响，同时研究了与 2,4,6-三甲基苯酚和 2,6-二叔丁基苯酚在甲苯和γ-戊内酯。对于某些酚类，还研究了自聚集对动力学参数的影响。
• Oxygen-hydrogen bond dissociation energies in para-substituted phenols
  作者：P. Mulder、O. W. Saastad、D. Griller

  DOI：10.1021/ja00220a088

  日期：1988.6
• Kinetic Solvent Effects on Hydrogen-Atom Abstractions:  Reliable, Quantitative Predictions via a Single Empirical Equation¹
  作者：Darren W. Snelgrove、Janusz Lusztyk、J. T. Banks、Peter Mulder、K. U. Ingold

  DOI：10.1021/ja002301e

  日期：2001.1.1

  The rate of hydrogen-atom abstraction from XH by a radical, Y-., can be solvent-dependent. In many cases, the kinetic solvent effect (KSE) is directly related to hydrogen-bonding interactions between XH and the solvent. The relative hydrogen-bond acceptor (HBA) properties of solvents are given by beta (H)(2) constants of Abraham et al. (Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Morris, J. J.; Taylor, P. J. J. Chem. Soc. Perkin Trans. 2 1990, 521-529). Room-temperature rate constants for hydrogen-atom abstraction, k(XH/Y).(S), have been determined in a number of solvents, S, where XH refers to several substituted phenols, tert-butyl hydroperoxide or aniline and Y-. is a tert-alkoxyl radical. In all cases, plots of log(k(XH/Y).(S)/M-1 s(-1)) versus beta (H)(2) gave excellent linear correlations, the slopes of which, M-XH, were found to be proportional to the hydrogenbond-donating (HBD) ability of XH, as scaled with alpha (H)(2) parameters of Abraham et al. (Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem,. Soc., Perkin Trans. 2 1989, 699-711), with M-XH = - 8.3 alpha (H)(2). This leads to a general empirical equation which quantifies KSEs at room log temperature : k(XH/Y).(S) = log k(XH/Y).(O) - 8.3 alpha (H)(2)beta (H)(2), where k(XH/Y).(O) refers to the rate constant in a non-HBA solvent for which beta (H)(2) = 0, generally a saturated hydrocarbon. Since M-XH depends only on XH, rate constants for hydrogen-atom abstraction from XH by any Y-. can be accurately predicted in any of the several hundred known or measured. HBA solvents can have profound effects on some of the reactions and thermodynamic properties of hydroxylic substrates including: (i) reaction product profiles (ii) antioxidant activities, (iii) Hammett-type correlations, and (iv) O-H bond dissociation enthalpies. Finally, literature data (Nielsen, M. F.; Hammerich, O. Acta Chem. Scand, 1992, 46, 883-896) on KSEs for two proton-transfer reactions are shown to be correlated by the same equation which correlates KSEs for hydrogen-atom transfers.