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

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.

Graphical abstractTwo novel pentacyanoferrate(II) complexes with biologically active ligands of the pyridinium-4-aldoxime type have been prepared. Both the ligands and their complexes were characterized in solution and as solids by various spectroscopic methods.Figure optionsDownload full-size imageDownload as PowerPoint slide