4,4′-dimethyl-3,3′-dinitro-2,2′-hydrazobipyridine | 640278-72-4

• 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: 4,4′-dimethyl-3,3′-dinitro-2,2′-hydrazobipyridine
• 英文别名: 4,4'-dimethyl-3,3'-dinitro-2,2'-hydrazobipyridine；4,4'-dimethyl-3,3'-dinitro-2,2'-hydrazopyridine
• CAS: 640278-72-4
• 化学式: C₁₂H₁₂N₆O₄
• 分子量: 304.265
• InChiKey: SKJVCSLWUUVUDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.35
• 重原子数：
  22.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  136.12
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  4,4′-dimethyl-3,3′-dinitro-2,2′-hydrazobipyridine 在 硝酸 作用下， 以74.2%的产率得到(2E)-4,4'-dimethyl-3,3'-dinitro-2,2'-azobipyridine
  参考文献：
  名称：

  Conformation of azo-bridge in 3,3′-dinitro-2,2′-azobipyridine and its 4,4′(or 5,5′ or 6,6′)-dimethyl-derivatives: Vibrational studies and DFT quantum chemical calculations

  摘要：

  Syntheses of 3,3'-dinitro-2,2'-azobipyridine and 4,4' (or 5,5' or 6,6')-dimethyl-3,3'-dinitro-2,2'-azobipyridine have been described. Molecular structures of these compounds have been determined and compared, to the basic compound, azobipyridine, reported by us earlier. The conformation of the azo-bond and other structural data are discussed in terms of substitution place of methyl chromophore. Fourier transform IR and Raman spectra of these compounds have been measured and analysed. The 6-311G (2d,2p) basis set with the B3LYP functional have been used to discuss the space conformation and dynamics of the studied compounds. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.saa.2014.02.050
• 作为产物：
  描述：

  4,4'-dimethyl-3,3'-dinitro-2,2'-azopyridine 在 硝酸 作用下， 生成 4,4′-dimethyl-3,3′-dinitro-2,2′-hydrazobipyridine
  参考文献：
  名称：

  Experimental and simulated 1H and 13C NMR spectra (GIAO/DFT approach) and molecular and crystal structures of dimethyl-dinitro-azo- and dimethyl-dinitro-hydrazo-pyridines

  摘要：

  The H-1 and C-13 NMR spectra of the 4,4'(or 6,6')-dimethyl-3,3'-dinitro-2,2'-azo- and hydrazo-pyridine have been measured in the solid state and solution. The spectral data have been analyzed on the basis of DFT quantum chemical calculations using the B3LYP/6-311G, 6-311++G and 6-311G** approaches. The structures of all molecules have been optimized starting from trans and cis molecular geometry and additionally from diimino form for hydrazoderivatives and compared to the XRD data. The optimization process always led to the trans - isomers. The influence of the azo-bond on the electronic properties of the whole system was analyzed. The role of the hydrogen bond in the structure stabilization of the hydrazo-derivatives has been discussed. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2011.07.056

文献信息

• The hydrazo-bond in 4,4′-dimethyl-3,3′-dinitro-2,2′-hydrazobipyridine – Crystal structure, conformation and vibrational characteristics
  作者：E. Kucharska、I. Bryndal、J. Hanuza、T. Lis

  DOI：10.1016/j.saa.2014.02.038

  日期：2014.6

  The crystal and molecular structure of 4,4'-dimethyl-3,3'-dinitro-2,2'-hydrazobipyridine have been determined by X-ray diffraction and quantum chemical OFT analysis. The title compound crystallizes in P (1) over bar space group, with one-half molecule in the asymmetric unit. The molecular structure is stabilized by intramolecular N-H center dot center dot center dot O hydrogen bonds. The molecules are linked by a combination of weak intermolecular C H center dot center dot center dot O interactions and also aromatic pi-pi stacking. The molecular structure of the studied compound has been determined using the DFT B3LYP/6-311G(2d,2p) approach and compared to that derived from X-ray studies. The IR and Raman wavenumbers have been calculated for the optimized geometry of a possible monomer structural model. The structural and vibrational properties of the intramolecular N-H center dot center dot center dot O interaction are described. (C) 2014 Elsevier B.V. All rights reserved.