Azobenzen-Radikalanion | 97732-44-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Azobenzen-Radikalanion
• 英文别名: azobenzene radical anion
• CAS: 97732-44-0
• 化学式: C₁₂H₁₀N₂
• 分子量: 182.225
• InChiKey: QBKLGALCXXAPJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  Azobenzen-Radikalanion 在 溶剂黄146 作用下， 生成 hydrazobenzene radical
  参考文献：
  名称：

  Gas-phase chemistry of the negative ions derived from azo- and hydrazobenzene

  摘要：

  The proton affinities of the azobenzene radical anion and the conjugate base of hydrazobenzene have been determined to be 1465 kJ mol-1 and 1514 kJ mol-1, respectively, with the use of a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer equipped with an external ion source. The proton affinities lead in combination with a measured electron affinity of azobenzene (55 kJ mol-1) to a N-H bond dissociation energy (BDE) of 306 kJ mol-1 for hydrazobenzene while the N-H BDE of the PhNHNPh radical is estimated to be 208 kJ mol-1. The difference between the N-H BDE values of 98 kJ mol-1 approximates the pi-bond energy of the nitrogen-nitrogen bond in azobenzene. The reaction of the PhNNBARPh and PhNHNBARPh ions with derivatives of trifluoroacetic acid are characterized. The occurrence of dissociative electron transfer instead of S(N)2 substitution in reactions of the azobenzene radical anion with halogen-substituted methanes is discussed.

  DOI：

  10.1021/jo00002a023
• 作为产物：
  描述：

  1,2-二苯肼 在 氧气 、 高氯酸四乙基铵 作用下， 以 二甲基亚砜 为溶剂， 生成 Azobenzen-Radikalanion
  参考文献：
  名称：

  超氧离子氧化取代肼：1,2-二苯肼自动氧化的起始步骤

  摘要：

  L'ion hyperoxyde en milieu aprotique et en phasegazeuse reagit avec des hydrazines dissubstituees-1,2 pour donner le Radical anionique du compose azoique 通讯员

  DOI：

  10.1021/ja00329a007

文献信息

• Investigation of the Direct and Indirect Reduction Processes of Some Disulfides by Electrochemical Means.
  作者：Torben Bo Christensen、Kim Daasbjerg、P. Valentin-Hansen、E. B. Pedersen、Kari Rissanen、Wenjun Shi、Stenbjörn Styring、Cecilia Tommos、Kurt Warncke、Bryan R. Wood

  DOI：10.3891/acta.chem.scand.51-0307

  日期：——

  The free energy relationship for the reaction between aromatic radical anions A(.-) having about the same intrinsic barrier and three disulfides RSSR (diphenyl disulfide, dimethyl disulfide and di-tert-butyl disulfide) in N,N-dimethylformamide has been obtained. For each RSSR second-order rate constants were measured electrochemically in the interval 10(-3)-10(-5) M(-1) s(-1) by changing the nature of A(.-) and thereby the driving force. In the case of diphenyl disulfide the standard potential E(RSSR/RSSR.-)degrees and the self-exchange reorganization energy lambda(0) of the RSSR/RSSR(.-) couple could be extracted from the free energy relationship to values of -1.4 (+/-0.1) V vs. SCE and 65 kcal mol(-1), respectively. This knowledge may be combined with the kinetic features of the heterogeneous reduction process of diphenyl disulfide to obtain, among other parameters, the standard heterogeneous rate constant. The cleavage rate constant k(c) of the corresponding radical anion was estimated from kinetic measurements to be about 5 x 10(8) s(-1). No such information was accessible for the aliphatic disulfides due to a high self-exchange energy of the RSSR/RSSR(.-) couple but still a maximum value of k(c) could be determined at 2 x 10(8) s(-1). The minimum values of E(RSSR/RSSR.-)degrees and lambda(0) were estimated to be -1.9 V vs. SCE and 75 kcal mol(-1) and -2.2 V vs. SCE and 75 kcal mol(-1) for dimethyl disulfide and di-tert-butyl disulfide, respectively.
• Costisella, Burkhard; Gross, Hans; Jeroschewski, Paul, Phosphorus and Sulfur and the Related Elements, 1987, vol. 29, p. 159 - 164
  作者：Costisella, Burkhard、Gross, Hans、Jeroschewski, Paul、Keitel, Iris、Schwarz, Karl-Heinz

  DOI：——

  日期：——
• Oxidation of substituted hydrazines by superoxide ion: the initiation step for the autoxidation of 1,2-diphenylhydrazine
  作者：Thomas S. Calderwood、Carolyn L. Johlman、Julian L. Roberts、Charles L. Wilkins、Donald T. Sawyer

  DOI：10.1021/ja00329a007

  日期：1984.8

  L'ion hyperoxyde en milieu aprotique et en phase gazeuse reagit avec des hydrazines disubstituees-1,2 pour donner le radical anionique du compose azoique correspondant

  L'ion hyperoxyde en milieu aprotique et en phasegazeuse reagit avec des hydrazines dissubstituees-1,2 pour donner le Radical anionique du compose azoique 通讯员
• Gas-phase chemistry of the negative ions derived from azo- and hydrazobenzene
  作者：Steen Ingemann、Roel H. Fokkens、Nico M. M. Nibbering

  DOI：10.1021/jo00002a023

  日期：1991.1

  The proton affinities of the azobenzene radical anion and the conjugate base of hydrazobenzene have been determined to be 1465 kJ mol-1 and 1514 kJ mol-1, respectively, with the use of a Fourier transform ion cyclotron resonance (FT-ICR) mass spectrometer equipped with an external ion source. The proton affinities lead in combination with a measured electron affinity of azobenzene (55 kJ mol-1) to a N-H bond dissociation energy (BDE) of 306 kJ mol-1 for hydrazobenzene while the N-H BDE of the PhNHNPh radical is estimated to be 208 kJ mol-1. The difference between the N-H BDE values of 98 kJ mol-1 approximates the pi-bond energy of the nitrogen-nitrogen bond in azobenzene. The reaction of the PhNNBARPh and PhNHNBARPh ions with derivatives of trifluoroacetic acid are characterized. The occurrence of dissociative electron transfer instead of S(N)2 substitution in reactions of the azobenzene radical anion with halogen-substituted methanes is discussed.