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Syntheses, structures and properties of isonicotinamidium, thionicotinamidium, 2- and 3-(hydroxymethyl)pyridinium nitrates

Zuzana Lukačovičová, Darina Lacková, Michal Brienik, Iveta Ondrejkovičová, Ondrej Záborský, Jana Doháňošová, and Marian Koman

Department of Inorganic Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology in Bratislava, Radlinského 9, 812 37 Bratislava, Slovakia



Abstract: New salts containing cations of selected pyridine derivatives of the composition [pyH]NO3, where py is 2-pyridylmethanol (2-(hydroxymethyl)pyridine, 2pm), 3-pyridylmethanol (3-(hydroxymethyl) pyridine, 3pm), isonicotinamide (4-(aminocarbonyl)-pyridine, inia) and thionicotinamide (4- (aminothiocarbonyl)pyridine, tnia) were synthesised using two methods. By the first method, the above salts were obtained from reaction mixtures prepared from Fe(NO3)3 ·9H2O and the appropriate pyridine derivative py in ethanol without the addition of acids. The protons required for protonation of the given pyridine derivatives are formed by the protolytic reaction of [Fe(H2O)6]3+, which acts as a cationic Brønstedt acid. These cations are present in the solid state of Fe(NO3)3 · 9H2O as well as in its solutions. Under the second procedure, the salts were prepared by a direct reaction of the selected pyridine derivative py with a diluted solution of HNO3. The first method affords crystals with lower yields but the second method produces microcrystals with higher yields. All the compounds were characterised by elemental analysis, infrared and NMR spectroscopic analyses and [3pmH]NO3 and [2pmH]NO3 by X-ray structure analysis also. [3pmH]NO3 crystallises in the monoclinic and [2pmH]NO3 in the triclinic system.

Keywords: pyridinium derivatives – nitrate – structural study – IR spectra – NMR spectroscopy

Full paper is available at

DOI: 10.1515/chempap-2015-0105


Chemical Papers 69 (8) 1093–1100 (2015)

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