N-methyl-4-pyridinealdoxime chloride | 58822-12-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-methyl-4-pyridinealdoxime chloride
• 英文别名: 4-pyridinealdoxime methchloride；PAM4-Cl；1-Methyl-4-(nitrosomethylidene)-1,4-dihydropyridine--hydrogen chloride (1/1)；1-methyl-4-(nitrosomethylidene)pyridine;hydrochloride
• CAS: 58822-12-1
• 化学式: C₇H₉N₂O*Cl
• 分子量: 172.614
• InChiKey: UJHFWIZEBFVUAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.68
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  36.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090

反应信息

• 作为产物：
  描述：

  4-PAM 在 盐酸 作用下， 以 甲醇 为溶剂， 以42%的产率得到N-methyl-4-pyridinealdoxime chloride
  参考文献：
  名称：

  Spectroscopic and structural insights into N-substituted pyridinium-4-aldoximes and their pentacyanoferrate(II) complexes

  摘要：

  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.

  DOI：

  10.1016/j.poly.2012.07.077

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.