3-氯苯酚自由基 | 54560-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-氯苯酚自由基
• 英文名称: 3-chlorophenoxyl radical
• 英文别名: 3-Chlorophenol radical；3-chlorophenoxyl；3-chloro-phenyloxyl
• CAS: 54560-44-0
• 化学式: C₆H₄ClO
• 分子量: 127.55
• InChiKey: JZSAROMFCRBUBD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  1
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  3-氯苯酚 在 1,1-二苯-2-苦基肼 作用下， 以 正庚烷 为溶剂， 生成 3-氯苯酚自由基
  参考文献：
  名称：

  Kinetic Solvent Effects on Hydrogen-Atom Abstractions:  Reliable, Quantitative Predictions via a Single Empirical Equation¹

  摘要：

  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.

  DOI：

  10.1021/ja002301e

文献信息

• Phenolic hydrogen abstraction by the triplet excited state of thiochromanone: a laser flash photolysis study
  作者：Alessandra M. Ribeiro、Ada Ruth Bertoti、José Carlos Netto-Ferreira

  DOI：10.1590/s0103-50532010000600017

  日期：——

  Triplet ketones are known to oxidize biological substrates which can lead to damage of several biomolecules such as amino acids, nucleosides and DNA. As part of our systematic study on the interaction between carbonyl compounds and phenols, the triplet reactivity of thiochromanone (1) towards substituted phenols, in acetonitrile, was investigated employing the laser flash photolysis technique. The

  已知三重态酮会氧化生物底物，这会导致几种生物分子（例如氨基酸，核苷和DNA）的破坏。作为我们对羰基化合物与苯酚之间相互作用的系统研究的一部分，使用激光闪光光解技术研究了硫代苯并二氢吡喃酮（1）对乙腈中取代苯酚的三重反应性。猝灭速率常数为（1.1±0.1）×108 L mol-1 s-1（4-氰基苯酚）至（5.8±1.0）×109 L mol-1 s-1（对苯二酚）。三重态1与含极性取代基的酚反应的哈米特图得出反应常数ρ= -0.90。
• Effect of ring substitution on the photochemistry of .alpha.-(aryloxy)acetophenones
  作者：J. C. Netto-Ferreira、I. G. J. Avellar、J. C. Scaiano

  DOI：10.1021/jo00288a019

  日期：1990.1