| 28173-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• CAS: 28173-38-8
• 化学式: C₉H₅O₂
• 分子量: 145.137
• InChiKey: QPJWCRFUDBJPGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  18.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  Phenylpropiolyl-peroxid 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Further spectroscopic and kinetic studies on carbonyloxyl radicals

  摘要：

  UV-visible absorption spectra and kinetic data obtained at room temperature are reported for three (alkenylcarbonyl)oxyls: trans-(CH3)3CCH = CHC(O)O., 1a; trans-C6H5CH = CHC(O)O., 1b; (CH3)2C = CHC(O)O., 1c; and two (alkynylcarbonyl)oxyls: (CH3)3CC = CC(O)O., 2a; C6H5C = CC(O)O., 2b. Rate constants for decarboxylation of 1a, 1b, 2a, and 2b are estimated to be less-than-or-equal-to 1.1 x 10(7), 1 x 10(6), 5 x 10(5) and 2 x 10(5) s-1, respectively. The first-order decay of 1c would appear to occur primarily by an intramolecular H atom abstraction, k approximately (2 +/- 1) x 10(7) s-1. The (alkynylcarbonyl)oxyls are more reactive than the (alkenylcarbonyl)oxyls in a variety of H atom abstraction reactions, e.g., with c-C6H12, and addition reactions, e.g., with C6H5CH = CH2. Combining the present and earlier5-7 kinetic data for carbonyloxyls yields the following order of decreasing reactivity for hydrogen abstraction and addition reactions: RC = CC(O)O. greater-than-or-equal-to ROC(O)O. > RR'C = CHC(O)O. greater-than-or-equal-to C6H5C(O)O. The reactivities of meta- and para-substituted aroyloxyls can be correlated with the intrinsic acidities and with the pK(a)'s of the corresponding benzoic acids, reactivity increasing with acid strength.

  DOI：

  10.1021/jo00007a029

文献信息

• Further spectroscopic and kinetic studies on carbonyloxyl radicals
  作者：H. G. Korth、J. Chateauneuf、J. Lusztyk、K. U. Ingold

  DOI：10.1021/jo00007a029

  日期：1991.3

  UV-visible absorption spectra and kinetic data obtained at room temperature are reported for three (alkenylcarbonyl)oxyls: trans-(CH3)3CCH = CHC(O)O., 1a; trans-C6H5CH = CHC(O)O., 1b; (CH3)2C = CHC(O)O., 1c; and two (alkynylcarbonyl)oxyls: (CH3)3CC = CC(O)O., 2a; C6H5C = CC(O)O., 2b. Rate constants for decarboxylation of 1a, 1b, 2a, and 2b are estimated to be less-than-or-equal-to 1.1 x 10(7), 1 x 10(6), 5 x 10(5) and 2 x 10(5) s-1, respectively. The first-order decay of 1c would appear to occur primarily by an intramolecular H atom abstraction, k approximately (2 +/- 1) x 10(7) s-1. The (alkynylcarbonyl)oxyls are more reactive than the (alkenylcarbonyl)oxyls in a variety of H atom abstraction reactions, e.g., with c-C6H12, and addition reactions, e.g., with C6H5CH = CH2. Combining the present and earlier5-7 kinetic data for carbonyloxyls yields the following order of decreasing reactivity for hydrogen abstraction and addition reactions: RC = CC(O)O. greater-than-or-equal-to ROC(O)O. > RR'C = CHC(O)O. greater-than-or-equal-to C6H5C(O)O. The reactivities of meta- and para-substituted aroyloxyls can be correlated with the intrinsic acidities and with the pK(a)'s of the corresponding benzoic acids, reactivity increasing with acid strength.