Benzenamine, 4-chloro-N-[(2,4-dinitrophenyl)methylene]-, (Z)- | 149742-64-3

• 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: Benzenamine, 4-chloro-N-[(2,4-dinitrophenyl)methylene]-, (Z)-
• 英文别名: 4-chloro-N-(2,4-dinitro-benzyliden)-aniline；4-Chlor-N-(2,4-dinitro-benzyliden)-anilin；2.4-Dinitro-benzaldehyd-(4-chlor-anil)
• CAS: 149742-64-3
• 化学式: C₁₃H₈ClN₃O₄
• 分子量: 305.677
• InChiKey: TXKLNZCJIZZWKW-OVCLIPMQSA-N

物化性质

• 沸点：
  480.5±45.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  98.64
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2,4-二硝基甲苯 在 乙醇 、 sodium carbonate 、 溶剂黄146 作用下， 生成 Benzenamine, 4-chloro-N-[(2,4-dinitrophenyl)methylene]-, (Z)-
  参考文献：
  名称：

  Bennett; Pratt, Journal of the Chemical Society, 1929, p. 1467

  摘要：

  DOI：

文献信息

• Downey; Lowy, Journal of the American Chemical Society, 1923, vol. 45, p. 1062
  作者：Downey、Lowy

  DOI：——

  日期：——
• Mechanism of thermal Z/E isomerization of substituted N-benzylideneanilines. Nature of the activated complex with an sp-hybridized nitrogen atom
  作者：Tsutomu Asano、Hiroyuki Furuta、Hans Joerg Hofmann、Renzo Cimiraglia、Yuho Tsuno、Mizue Fujio

  DOI：10.1021/jo00068a042

  日期：1993.7

  In order to study the mechanism of thermal geometrical isomerization involving a sp2-hybridized nitrogen atom, kinetic effects of substituent, solvent, and pressure were studied in substituted N-benzylideneanilines. The effect of the substituent on the aniline moiety was almost independent of the electronic nature of the benzylidene group, and the results could be described satisfactorily by log (k/k(o)) = rho[sigma-degrees + r+(sigma+-sigma-degrees)+ r-(sigma--sigma-degrees)], except for the 4-(dimethylamino) group. The r- values were more than twice as large as r+, suggesting strongly that the aniline ring is in conjugation not with the carbon-nitrogen pi bond but with the nitrogen lone pair in the transition state. The lower activation enthalpies and fairly large negative activation entropies observed in N-(4-X-benzylidene)4-nitroanilines also support this view. When a dimethylamino group exists in the 4-position of the aniline ring, the rate constants observed were larger than that expected from the above equation. This deviation suggests the existence of a reaction route where the two phenyl groups become coplanar in the transition state. Ab initio calculations on selected N-phenylformaldimines and N-benzylideneanilines were performed to characterize the actual relation between both reaction possibilities as alternative and parallel routes, respectively. On the basis of the experimental data, the rate constants for the two inversion isomerizations were estimated by assuming parallel reactions for three cases.
• Bennett; Pratt, Journal of the Chemical Society, 1929, p. 1467
  作者：Bennett、Pratt

  DOI：——

  日期：——