C-nitrosomesitylene dimer | 100046-00-2

• 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: C-nitrosomesitylene dimer
• 英文别名: [MesNO]₂；dimesityl-diazene dioxide；Dimesityl-diazen-dioxid；oxo-(2,4,6-trimethyl-N-oxidoanilino)-(2,4,6-trimethylphenyl)azanium
• CAS: 100046-00-2；129615-67-4；129615-69-6
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: WJNNDZMCMDEEQQ-UHFFFAOYSA-N

物化性质

• 沸点：
  462.4±55.0 °C(Predicted)
• 密度：
  1.102±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  C-nitrosomesitylene dimer 以 四氯化碳 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 生成 1,3,5-三甲基-2-亚硝基苯
  参考文献：
  名称：

  Pressure Effect on Dimerization Equilibria of a Series of Substituted Nitrosobenzenes in Solution

  摘要：

  AbstractThe effect of pressure was studied on the dimerization reactions of six di‐ and tri‐substituted nitrosobenzenes in carbon tetrachloride at 25°C. The obtained configurational volume changes for the prototype one bond formation reactions are in the range of —17 to —21 cm3 mol−1 at 6.13 MPa. The volume changes were interpreted in terms of the perturbation theory of liquid; they were dominated by the volume change in the reference system composed of hard spheres. Small differences between the observed and theoretical reference volume changes were ascribed to the perturbation due to electrostatic interactions between the solute and solvent; the perturbation volume changes were estimated by the Kirkwood theory of dipolar solvation.

  DOI：

  10.1002/bbpc.198800009
• 作为产物：
  描述：

  1,3,5-三甲基-2-亚硝基苯 以 四氯化碳 为溶剂， 25.0 ℃ 、100.0 kPa 条件下， 生成 C-nitrosomesitylene dimer
  参考文献：
  名称：

  Pressure Effect on Dimerization Equilibria of a Series of Substituted Nitrosobenzenes in Solution

  摘要：

  AbstractThe effect of pressure was studied on the dimerization reactions of six di‐ and tri‐substituted nitrosobenzenes in carbon tetrachloride at 25°C. The obtained configurational volume changes for the prototype one bond formation reactions are in the range of —17 to —21 cm3 mol−1 at 6.13 MPa. The volume changes were interpreted in terms of the perturbation theory of liquid; they were dominated by the volume change in the reference system composed of hard spheres. Small differences between the observed and theoretical reference volume changes were ascribed to the perturbation due to electrostatic interactions between the solute and solvent; the perturbation volume changes were estimated by the Kirkwood theory of dipolar solvation.

  DOI：

  10.1002/bbpc.198800009

文献信息

• Reactions between Organomercury Compounds and Nitrosyl Compounds^1,2
  作者：Lee Irvin Smith、F. Lowell Taylor

  DOI：10.1021/ja01315a043

  日期：1935.12
• Reactions of Organozinc Thiolates with Nitrosonium Ion: <i>C</i>-Nitroso Formation by Possible Transnitrosation
  作者：Julia Kozhukh、Juliana Fedoce Lopes、Hélio F. Dos Santos、Stephen J. Lippard

  DOI：10.1021/om300922m

  日期：2012.12.10

  The organometallic complexes [ZnPAThEt] and [ZnPAThMes], where PATh is 2-methyl-1-[methyl-(2-pyridin-2-yl-ethyl)amino]propane-2-thiolate, were prepared and their reactions with NOBF4 investigated. Formation of C-nitrosoethane and C-nitrosomesitylene, respectively, was established, and structural characterization of the latter by X-ray crystallography conclusively proved the dimeric nature of [MesNO](2) in the solid state. A transnitrosation pathway for C-nitroso formation is proposed based on theoretical calculations.
• Activation Volume for Dimerization Reaction of 2,4,6-Trimethylnitrosobenzene in Solution
  作者：Y. Yoshimura、M. Nakahara

  DOI：10.1002/bbpc.198800010

  日期：1988.1

  AbstractThe effect of pressure on the rate and equilibrium constants for the dimerization reaction of 2,4,6‐trimethylnitrosobenzene in acetonitrile was studied up to 196 MPa at 25°C in order to examine whether the dynamical effect on the reaction process in solution can be neglected as assumed in the transition state theory. All the rate constants relevant to the dimerization were determined by the pressure relaxation method. The configurational reaction volume for the dimerization and the activation volume for the dissociation were —17.4 ± 0.7 and + 5.1 ± 0.3 cm3 mol 1 at 98 MPa, respectively. The experimental results were in reasonable agreement with the theoretical ones that were calculated for the model system composed of hard spheres according to the liquid theory and the transition state theory. The dynamical effect on the activation volume was not detected in the present reaction system.