1-苯甲酰甲基-4-羟基亚胺甲酰基吡啶鎓氯化物 | 19340-18-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-苯甲酰甲基-4-羟基亚胺甲酰基吡啶鎓氯化物
• 英文名称: 1-phenacylpyridinium-4-aldoxime chloride
• 英文别名: N-phenacylpyridinium-4-aldoxime chloride；FEPA4-Cl；FEPA-4；2-[4-(Nitrosomethylidene)pyridin-1(4H)-yl]-1-phenylethan-1-one--hydrogen chloride (1/1)；2-[4-(nitrosomethylidene)pyridin-1-yl]-1-phenylethanone;hydrochloride
• CAS: 19340-18-2
• 化学式: C₁₄H₁₃N₂O₂*Cl
• 分子量: 276.722
• InChiKey: UPKWZZLZMIFLQV-UHFFFAOYSA-N

物化性质

• 熔点：
  209.5-210.5 °C

计算性质

• 辛醇/水分配系数(LogP)：
  3.966
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  53.5
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  trisodium aquapentacyanoferrate 、 1-苯甲酰甲基-4-羟基亚胺甲酰基吡啶鎓氯化物 以 水 为溶剂， 生成 [Fe(CN)₅(N-phenacylpyridinium-4-aldoxime)]^-2
  参考文献：
  名称：

  Burger, N.; Hankonyi, V.; Smeric, Z., Zeitschrift fur Physikalische Chemie (Leipzig), 1990, vol. 271, # 4, p. 787 - 791

  摘要：

  DOI：
• 作为产物：
  描述：

  4-吡啶甲醛肟 、 alpha-氯乙酰苯 以 乙醇 为溶剂， 反应 168.0h， 以70.4%的产率得到1-苯甲酰甲基-4-羟基亚胺甲酰基吡啶鎓氯化物
  参考文献：
  名称：

  Preparation, characterization and reactivity of 1-benzylpyridinium-4-aldoxime chloride and 1-phenacylpyridinium-4-aldoxime chloride and their complexes with the aquapentacyanoferrate(II) ion

  摘要：

  A detailed structural characterization of the biologically active 1-benzylpyridinium-4-aldoxime chloride and 1-phenacylpyridinium-4-aldoxime chloride was performed using NMR and vibrational and electronic spectroscopy, as well as X-ray diffraction. The complexes of these compounds with the aquapentacyanoferrate(II) ion were examined in solution, isolated as solids and characterized by elemental analysis, electronic, FT-IR and NMR spectral data. They were found to be mononuclear substituted pentacyanoferrates(II) containing the aldoxime group coordinated to the iron through the nitrogen atom. The complexes were also precipitated in the form of the respective zinc salts; the analysis of these complexes revealed a molar Fe/Zn ratio of 1, thus confirming the charge of the complex anions to be -2. The ionization constants of the aldoxime group in the free ligands and in the respective cyano complexes were also determined. Despite the presence of two donor sites in 1-phenacylpyridinium-4-aldoxime chloride, only the aldoxime group was found to be reactive. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.01.041

文献信息

• Spectroscopic and structural insights into N-substituted pyridinium-4-aldoximes and their pentacyanoferrate(II) complexes
  作者：Blaženka Foretić、Igor Picek、Vladimir Damjanović、Danijela Cvijanović、Ivana Pulić、Boris-Marko Kukovec、Dubravka Matković-Čalogović

  DOI：10.1016/j.poly.2012.07.077

  日期：2013.3

  Comparative kinetic and equilibrium studies on the formation and dissociation of three mono- and one bis-pyridinium-4-aldoxime pentacyanoferrate(II) complexes have been carried out in aqueous solutions at 25 degrees C and I = 0.1 M. The synthesis, spectroscopic and thermal characterization of a new N-methylpyridinium-4-aldoxime pentacyanoferrate(II) complex is presented. The obtained values for the equilibrium constants, identified as apparent formation constants (beta(f)/M-1) along with kinetic parameters, the formation (k(f)/M-1 s(-1)) and dissociation (k(d)/s(-1)) rate constants indicated the behaving of all protonated pyridinium-4-aldoximes as weak pi-acceptors. The pH-dependence of the dissociation rates has been analyzed in terms of ionization abilities of the coordinated ligands. The magnitude of the dissociation rates suggested that both protonated and deprotonated ligand forms are effective sigma-donors that bind to the [Fe(CN)(5)](3-) moiety through the nitrogen atom. The deprotonation of the coordinated aldoxime group leads to the reduced lability of the complexes due to increased sigma-donor capability of aldoximato nitrogen causing the strengthened of the iron(II)-nitrogen bond. The values of dissociation activation parameters, Delta H-double dagger and Delta S-double dagger, are found to be consistent with the S(N)1 dissociative type of mechanism. The spectroscopic data (FT-IR, NMR and UV-Vis) of the isolated coordinated pentacyanoferrates(II) conforms with the weak pi-acceptor properties of the pyridinium-4-aldoxime ligands. A detailed structural characterization of the iodide and chloride salt of N-methylpyridinium-4-aldoxime was also presented using NMR, FT-IR and UV-Vis spectroscopy, as well as X-ray diffraction. (C) 2012 Elsevier Ltd. All rights reserved.