β-bromotetraphenylporphine | 52353-91-0

• 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: β-bromotetraphenylporphine
• 英文别名: 2,7,12,17-tetrabromo-5,10,15,20-tetraphenyl-porphyrin；2,7,12,17-tetrabromo-5,10,15,20-tetraphenyl-21H,23H-porphine
• CAS: 52353-91-0
• 化学式: C₄₄H₂₆Br₄N₄
• 分子量: 930.333
• InChiKey: UZUISDVWKPKZEB-SJUVESBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.29
• 重原子数：
  52.0
• 可旋转键数：
  4.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.36
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  zinc diacetate 、 β-bromotetraphenylporphine 以 N,N-二甲基甲酰胺 为溶剂， 生成 zinc 2,7,12,17-tetrabromo-5,10,15,20-tetraphenylporphyrine
  参考文献：
  名称：

  摘要：

  Extra coordination of zinc complexes of bromo-substituted tetraphenylporphyrins was studied by spectrophotometry. It was found that the stability of complexes thus formed markedly increases upon beta-bromo-substitution in tetraphenylporphine. The effects of electronic and structural factors on the extra coordination were discussed. The stability constants of complexes formed by zinc porphyrins with organic bases were calculated, and the electronic absorption spectra of porphyrins in toluene and in other organic solvents were studied.

  DOI：

  10.1023/a:1020030714257
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 生成 β-bromotetraphenylporphine
  参考文献：
  名称：

  First X-ray crystal structure of a lanthanide(iii) monoporphyrinic complex using non-planar porphyrin rings

  摘要：

  在首次合成镧系(III)卟啉 23 年后，报告了[Tb III (β-Cl 8 tpp)(O 2 CMe)(Me 2 SO 2 ]的 X 射线晶体结构；描述了四种卤代卟啉 H 2 (β-X n tpp) (X = Cl 或 Br, n = 4 或 8) 的合成路线，并与相应的[Tb III (β-X n tpp)(O 2 CMe)] 进行了比较； 将 Tb III 复合物的高度畸变结构与类似的全卤化卟啉复合物进行了比较；还报告了溴化游离碱的 X 射线结构。

  DOI：

  10.1039/a608013h

文献信息

• Comparative Study of Structure−Properties Relationship for Novel β-Halogenated Lanthanide Porphyrins and Their Nickel and Free Bases Precursors, as a Function of Number and Nature of Halogens Atoms
  作者：G. A. Spyroulias、A. P. Despotopoulos、C. P. Raptopoulou、A. Terzis、D. de Montauzon、R. Poilblanc、A. G. Coutsolelos

  DOI：10.1021/ic000738h

  日期：2002.5.1

  The synthetic route of partially beta-halogenated via a "metal-assisted" reaction and perhalogenated terbium complexes is described. This protocol allows the facile insertion of the halogens (bromines or chlorides) to the porphyrin peripheral positions. The electronic absorption spectra and the redox potentials of the free porphyrins as well as the terbium complexes are dramatically affected as the number of halogen atoms increase. In fact, two antagonistic effects are responsible for that, the inductive and the distortion effects on the porphyrin ring. They result in a red shift for the Soret band and a stabilization/destabilization of the HOMOs/LUMOs which in turn is manifested by variations on the redox potentials. The novel crystal structure of the Ni(Cl8TPP) is discussed in great detail and compared with the previously reported structures of Tb(Cl8TPP) (OAc)(DMSO)(2).3PhCH(3).MeOH and H-2(Br8TPP), as well as with other perhalogenated nickel porphyrins available in the literature.
• ——
  作者：B. D. Berezin、T. V. Karmanova、T. V. Gromova、A. S. Semeikin

  DOI：10.1023/a:1021626127175

  日期：——

  Rate constants of zinc acetate complexation with 2,7,12,17-tetrabromo-5,10,15,20-tetraphenylporphine in toluene, pyridine, or acetic acid following the reaction H2TPP(beta-Br)(4) + Zn(Ac)(2) --> ZnTPP(beta-Br)(4) + 2HAc are determined at four temperatures in the interval of 298-328 K, and the activation energies and entropies are calculated. The effect of bromo-substitution in pyrrole fragments of a tetraphenylporphine molecule on the complexation kinetics and mechanism is discussed.
• Klyueva; Lomova; Berezin, Russian Journal of General Chemistry, 1997, vol. 67, # 4, p. 499 - 504
  作者：Klyueva、Lomova、Berezin

  DOI：——

  日期：——