Please cite this article as: L.S. Vojinović-Ješić, M.M. Radanović, M.V. Rodić, V. Živković-Radovanović, L.S. Jovanović, V.M. Leovac, Syntheses and characterization of 2-acetylpyridine-aminoguanidine and its copper(II) complexes: Crystallographical and antimicrobial study, Polyhedron (2016), doi: http://dx.
AbstractThe syntheses, physico-chemical and microbiological properties of the ligand, 2acetylpyridine-aminoguanidine dihydrogensulfate monohydrate and its five complexes with Cu(II) are described. The compounds were characterized by single crystal X-ray crystallography. Common fragments encountered in some of the structures were compared by r.m.s. overlay calculations as well as half-normal probability plots. In these complexes the chelate ligand is coordinated in its neutral form in a tridentate N 3 -coordination mode, via pyridine, azomethine and imino nitrogen atoms of the aminoguanidine fragment. In these complexes the Cu(II) ion is situated in moderately or severely distorted square-pyramidal surroundings. The antimicrobial activity of the ligand and the complexes were examined against 6 selected bacterial and 3 fungal strains.structural and antimicrobial properties of the ligand, 2-acetylpyridine-aminoguanidine dihydrogensulfate monohydrate and its Cu(II) complexes.
Experimental
Materials and physical measurementsAll commercially obtained reagent-grade chemicals were used without further purification. The ligand 2-acetylpyridine-aminoguanidine dihydrogenchloride, L·2HCl, was prepared according to a previously described procedure [18] with a slight modification.Elemental analyses (C, H, N and S) of the air-dried compounds were carried out by standard micro-methods in the Center for Instrumental Analyses, ICTN in Belgrade. The chlorine content was determined by potentiometric titration using AgNO 3 . The compound was combusted using the Schoeniger method [19] and the products were absorbed in a solution of H 2 O 2 and KOH. Molar conductivity measurements of freshly prepared 1 mM solutions were performed on a Jenway 4010 conductivity meter. IR spectra were recorded on a Nicolet Nexus 670 FTIR (Thermo Scientific) spectrophotometer in the range 400-4000 cm -1 by the KBr pellet technique. Electronic spectra of DMF solutions of the ligand and the complexes were recorded on a T80+UV-Vis spectrometer (PG Instruments, Ltd.), in the spectral range 270-1000 nm.
Syntheses
L·2HCl, 2-acetylpyridine-aminoguanidine dihydrogenchlorideAminoguanidine-hydrogencarbonate (3.4 g, 25 mmol) was dissolved in 25 mL 2N HCl. After the addition of 2-acetylpyridine (2.8 mL, 25 mmol) the reaction mixture was heated for 1 h. The obtained microcrystalline product was evaporated nearly to dryness, using hot air, filtered in vacuo and washed with MeOH. Yield: 4.37 g (70%). Single crystals of the ligand were obtained by recrystallization from warm MeOH. Anal. Calc. for C 8 H 13 N 5 Cl 2 : C, 38.43; H, 5.20; N, 28.01; Cl, 28.34. Found: C, 38.10; H, 5.47; N, 27.76; Cl,27.99%. Conductivity [Λ M /Ω −1 cm 2 mol −1 ]: 170 (in MeOH). Selected IR ba...