CuPc(4-Br)4(5-NO2)4 | 218303-19-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四吡咯及其衍生物
• 英文名称: CuPc(4-Br)4(5-NO2)4
• 英文别名: [Cu(Pc(5-NO2)4(4-Br)4)]；Copper;6,15,24,33-tetrabromo-7,16,25,34-tetranitro-2,11,20,29,37,38-hexaza-39,40-diazanidanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1(37),2,4,6,8,10,12,14,16,18,20,22,24,26,28(38),29,31,33,35-nonadecaene
• CAS: 218303-19-6
• 化学式: C₃₂H₈Br₄CuN₁₂O₈
• 分子量: 1071.65
• InChiKey: WWPWCZJPEUQPCX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.81
• 重原子数：
  57
• 可旋转键数：
  0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  263
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  CuPc(4-Br)4(5-NO2)4 在 硫酸 作用下， 生成 6,15,24,33-Tetrabromo-7,16,25,34-tetranitro-2,11,20,29,37,38,39,40-octazanonacyclo[28.6.1.13,10.112,19.121,28.04,9.013,18.022,27.031,36]tetraconta-1,3,5,7,9,11,13,15,17,19(39),20,22,24,26,28,30(37),31,33,35-nonadecaene
  参考文献：
  名称：

  摘要：

  Transformations of the complexes CuPc(4-NO2)(4), CuPe(4-Br)(4)(5-NO2)(4), (OH)AlRs(4-NO2)(4), and (OH)AlPc(4-Cl)(4)(5-NO2)(4) in concentrated sulfuric acid were studied by spectrophotometry. One protonated form of CuPc(4-Br)(4)(5-NO2)(4) and (OH)AlPc(4-NO2)(4) and two protonated forms of CuPc(4-NO2)(4) and (OH)AlPc(4-Cl)(4)(5-NO2)(4) were detected experimentally and also by ZINDO1 calculations. Step protonation constants of CuPc(4-NO2)(4) and (OH)AlPc(4-Cl)(4)(5-NO2)(4) were determined by quantum-chemical calculations and acid-base titration; these complexes can be regarded as weak bases with respect to H2SO4. The kinetics of dissociation of the complexes at the M-N bonds were studied. The rate of dissociation of the Cu(II) complexes and (OH)AlPc(4-NO2)(4) is proportional to [MPc(R)(n)] and [H3O+](2). The rate of dissociation of (OH)AlPc(4-Cl)(4)(5-NO2)(4) showed a weak extremal dependence on the composition of the medium, which was explained by change of its structure in 17.0 M H2SO4. The electronic effect of substituents on the reaction center was considered with account taken of a complex mechanism of activation and fine details of the molecular structure of macrocyclic complexes.

  DOI：

  10.1023/a:1020454912210
• 作为产物：
  描述：

  铜 、 4-溴-5-硝基-1,2-苯二甲腈 以 neat (no solvent) 为溶剂， 生成 CuPc(4-Br)4(5-NO2)4
  参考文献：
  名称：

  Bifunctional octasubstituted phthalocyanines. Synthesis and properties

  摘要：

  Data on the synthesis of bifunctional octasubstituted phthalocyanines are reported. Some specificities of their electronic absorption spectra, thermal stability, and other properties, depending on the substituent nature and central metal ion, are revealed.

  DOI：

  10.1134/s1070363207010215

文献信息

• Shishkina; Maizlish; Shaposhnikov, Russian Journal of General Chemistry, 1998, vol. 68, # 5, p. 813 - 817
  作者：Shishkina、Maizlish、Shaposhnikov、Smirnov

  DOI：——

  日期：——
• Bifunctional octasubstituted phthalocyanines. Synthesis and properties
  作者：G. P. Shaposhnikov、V. E. Maizlish、V. P. Kulinich

  DOI：10.1134/s1070363207010215

  日期：2007.1

  Data on the synthesis of bifunctional octasubstituted phthalocyanines are reported. Some specificities of their electronic absorption spectra, thermal stability, and other properties, depending on the substituent nature and central metal ion, are revealed.
• ——
  作者：T. N. Sokolova、T. N. Lomova、E. E. Suslova、S. V. Zaitseva、S. A. Zdanovich、V. E. Maizlish、O. V. Shishkina、G. P. Shaposhnikov

  DOI：10.1023/a:1020454912210

  日期：——

  Transformations of the complexes CuPc(4-NO2)(4), CuPe(4-Br)(4)(5-NO2)(4), (OH)AlRs(4-NO2)(4), and (OH)AlPc(4-Cl)(4)(5-NO2)(4) in concentrated sulfuric acid were studied by spectrophotometry. One protonated form of CuPc(4-Br)(4)(5-NO2)(4) and (OH)AlPc(4-NO2)(4) and two protonated forms of CuPc(4-NO2)(4) and (OH)AlPc(4-Cl)(4)(5-NO2)(4) were detected experimentally and also by ZINDO1 calculations. Step protonation constants of CuPc(4-NO2)(4) and (OH)AlPc(4-Cl)(4)(5-NO2)(4) were determined by quantum-chemical calculations and acid-base titration; these complexes can be regarded as weak bases with respect to H2SO4. The kinetics of dissociation of the complexes at the M-N bonds were studied. The rate of dissociation of the Cu(II) complexes and (OH)AlPc(4-NO2)(4) is proportional to [MPc(R)(n)] and [H3O+](2). The rate of dissociation of (OH)AlPc(4-Cl)(4)(5-NO2)(4) showed a weak extremal dependence on the composition of the medium, which was explained by change of its structure in 17.0 M H2SO4. The electronic effect of substituents on the reaction center was considered with account taken of a complex mechanism of activation and fine details of the molecular structure of macrocyclic complexes.