4-Nitrotoluene radical anion | 34509-96-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 4-Nitrotoluene radical anion
• 英文别名: p-nitrotoluene anion；1-methyl-4-nitro-benzene; radical anion；p-Methylnitrobenzolradikalanion
• CAS: 34509-96-1
• 化学式: C₇H₇NO₂
• 分子量: 137.138
• InChiKey: YWRFZFBZPUANMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  10.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  43.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-Nitrotoluene radical anion 在 水 、 dioxide titanium 、 异丙醇 作用下， 生成 4-硝基甲苯
  参考文献：
  名称：

  Photocatalytic Reduction of Nitroorganics over Illuminated Titanium Dioxide:  Electron Transfer between Excited-State TiO₂ and Nitroaromatics

  摘要：

  The present study investigates the steady-state photocatalytic reduction of methyl viologen and a suite of monosubstituted nitrobenzenes. Reduction was carried out in deoxygenated, illuminated aqueous slurries of titanium dioxide (Degussa P25) in the presence of a sacrificial electron donor, 2-propanol. Langmuir-Hinshelwood plots were obtained for the reduction of each compound and found to be linear, with an average correlation of 0.98 and with a standard deviation on the correlations of 0.02. The concentration independent rates for nitroaromatic reduction obtained from these plots were normalized against the rate of methyl viologen reduction, and the ratio was used to solve for the rate constant of nitroaromatic reduction, assuming a bimolecular model. The assumptions behind this procedure were tested by the use of the Marcus expression. Using the reorganization energy for the reaction as the fitting variable, it was possible to fit the measured rates to the predicted rates with a reorganization energy of 138 kJ/mol.

  DOI：

  10.1021/jp973224l
• 作为产物：
  描述：

  4-硝基甲苯 在 三乙胺 作用下， 以 乙腈 为溶剂， 生成 4-Nitrotoluene radical anion
  参考文献：
  名称：

  胺对4-取代硝基苯的光还原

  摘要：

  采用循环伏安法、EPR 光谱法和稳态光解法研究了三乙胺在乙腈中对 4 位具有给电子和吸电子取代基的硝基苯的还原作用。硝基化合物的电化学还原显示出对应于一个电子转移的可逆阴极波，并形成硝基苯自由基阴离子。还原电位与自由基阴离子的超精细氮耦合常数和4-取代基的供体-受体特性密切相关。在三乙胺存在下硝基化合物的光还原产生硝基苯自由基阴离子。EPR自旋捕获实验表明，α-氨基乙基自由基仅在具有给电子取代基的硝基苯的光解中形成。这些在胺存在下的化合物是甲基丙烯酸甲酯聚合反应的有效光引发剂。聚合速率随着胺浓度达到恒定值而增加。对于光漂白量子产率观察到类似的行为。这些结果表明，光漂白和导致自由基能够添加到单体中的反应来自硝基化合物的三重态与胺的相互作用，随后质子在双离子对内转移产生中性自由基。在没有单体的情况下，亚硝基苯似乎是主要产物。在吸电子取代硝基苯存在下的聚合反应可以忽略不计。这与缺乏α-氨基烷基自由基形成一致。

  DOI：

  10.1039/b314883a

文献信息

• Electron affinities from electron-transfer equilibria: A- + B = A + B-
  作者：Eric P. Grimsrud、Gary Caldwell、Swapan Chowdhury、Paul Kebarle

  DOI：10.1021/ja00302a005

  日期：1985.8

  L'etude est faite pour 34 composes, principalement des nitrobenzenes substitues, des quinones substituees et des molecules conjuguees contenant des atomes d'oxygene

  L'练习曲EST faite倾34层构成，principalement DES硝基苯subSTitues，脱醌subSTituees和des分子conjuguees contenant DES atomes D'OXYGENE
• Entropy changes and electron affinities from gas-phase electron-transfer equilibria: A- + B = A + B-
  作者：Swapan Chowdhury、Thomas Heinis、Eric P. Grimsrud、Paul Kebarle

  DOI：10.1021/j100403a037

  日期：1986.6
• Resonance Electron Capture Rate Constants for Substituted Nitrobenzenes
  作者：W. B. Knighton、R. S. Mock、D. S. McGrew、E. P. Grimsrud

  DOI：10.1021/j100065a036

  日期：1994.4

  We report here a new method for the determination of electron capture (EC) rate constants that utilizes a pulsed electron beam mass spectrometer. The method is first tested by measurements of the known dissociative electron capture rate constants for several halogenated methanes that have been extensively studied by other techniques. The resonance electron capture (REC) rate constants of nitrobenzene (NB) and 23 substituted nitrobenzenes (SNB's) are then determined for the first time at 125 degrees C in 10 Torr of methane buffer gas. The SNB's studied here include several sets of closely related structural isomers whose electron affinities (EA's) have been previously determined. It is shown that the REC rate constants of these compounds bear little systematic relationship with the EA's of these compounds. The REC rate constants of the SNB's are also compared with other previously reported characteristics associated with the negative ionization of these compounds, including their entropies of negative ionization, the lifetimes against autodetachment of their initially formed molecular anions, and the rates of autodetachment from electronically excited states of their molecular anions.
• Electron affinities of di- and tetracyanoethylene and cyanobenzenes based on measurements of gas-phase electron-transfer equilibria
  作者：Swapan. Chowdhury、Paul. Kebarle

  DOI：10.1021/ja00278a014

  日期：1986.9
• One-electron reduction of nitrobenzenes by .alpha.-hydroxyalkyl radicals via addition/elimination. An example of an organic inner-sphere electron-transfer reaction
  作者：V. Jagannadham、S. Steenken

  DOI：10.1021/ja00334a015

  日期：1984.10