Synthesis, characterization and crystal structure of square-pyramidal copper(II) complexes with pyridoxylidene aminoguanidine

Lalovic, M.; Vojinović-Ješić, Ljiljana S.; Jovanović, Ljiljana S.; Leovac, Vukadin M.; Češljević, Valerija I.; Divjaković, Vladimir

doi:10.1016/j.ica.2012.03.026

Cited by 21 publications

(19 citation statements)

References 15 publications

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“…Namely, in this peculiar case, PLTSC is coordinated via phenolic oxygen, azomethine nitrogen and thioamide sulfur atoms to one cooper center, thus forming two metallocycles: one fivemembered and one six-membered, whereas the oxygen atom of hydroxymethyl fragment is coordinated to another copper center in its apical position. Similar behavior is observed for structurally related ligands-pyridoxal semicarbazone in nickel(II) complex [33] and pyridoxal aminoguanidine in copper(II) complex [34]. Structure analysis showed also that ligands are coordinated in neutral zwitterionic form, i.e., they are deprotonated at the phenolic O1 and protonated at the pyridine N4 atoms.…”

Section: Resultssupporting

confidence: 71%

Synthesis, characterization and thermal behavior of copper(II) complexes with pyridoxal thiosemi (PLTSC)- and S-methylisothiosemicarbazone (PLITSC)

Vojinović-Ješić

Rodić

Holló

et al. 2015

J Therm Anal Calorim

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The syntheses of complexes of Cu(II) with biological active ligand, pyridoxal thiosemicarbazone (PLTSC) and its derivative, pyridoxal S-methylisothiosemicarbazone, are described. All coordination compounds were characterized by elemental analysis, molar conductivity and infrared spectra. The crystal and molec-is determined by single-crystal X-ray crystallography, too. The thermal decomposition of all the ligands and complexes was determined by simultaneous TG/DSC measurements. The decomposition mechanisms were compared and analyzed from the aspects of the relationships between the structures of the compounds and their thermal decomposition pattern.

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Section: Resultssupporting

confidence: 71%

Synthesis, characterization and thermal behavior of copper(II) complexes with pyridoxal thiosemi (PLTSC)- and S-methylisothiosemicarbazone (PLITSC)

Vojinović-Ješić

Rodić

Holló

et al. 2015

J Therm Anal Calorim

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“…1645 cm −1 ) compared to its position in the spectrum of the ligand (1684 cm −1 ) [11,14,33]. The band that may be ascribed to the vibrations of the guanido group appears at 1624 cm −1 in the ligand spectrum, but in the spectra of all the complexes it shows a negative shift of ~20 cm −1 [11,12].…”

Section: Ir and Electronic Spectramentioning

confidence: 97%

“…However, the number of structurally characterized complexes with these Schiff bases is still small. The most numerous are complexes of copper(II) with pyridoxilidene aminoguanidine [14] and salicylidene aminoguanidine [12,[15][16][17].…”

Section: Introductionmentioning

confidence: 99%

Syntheses and characterization of 2-acetylpyridine-aminoguanidine and its copper(II) complexes: Crystallographic and antimicrobial study

et al. 2016

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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...

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“…The aminoguanidine derivatives with aldehyde or keto group have been employed to prepare metal complexes for its biological activities in the research area of bioinorganic chemistry [1][2][3][4]. The title compound is a new aminoguanidine derivative and has been synthesized in a convenient approach in our work.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (E)-1-((1-(3,4-dimethoxyphenyl)ethyl)imino) guanidinium perchlorate, C11H17ClN4O6

Deng

2015

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialAll reagents and solvents obtained from commercial sources were used without further purification. Aminoguanidine hydrochloride (1.1 g, 10 mmol) was slowly added to a solution of 1-(3,4-dimethoxyphenyl)ethanone (1.8 g, 10 mmol) in 60 ml absolute ethanol. The reaction mixture was stirred for 10 hours under reflux, and then filtered after cooled down. The resulted white powder crystal was obtained as the product in yielding 88 %. After the filtrate was allowed to stand for three days, colourless, tabular crystals suitable for X-ray analysis were obtained. IR (KBr pellet, cm -1 ): 3540vs, 3409vs, 3082b, 1624s, 1520m, 1426s, 1227m, 1114m, 877w, 851s, 781w, 743w, 719s, 655m, 522w, 505w, 433w. Elemental analysis: found -C, 55.89%; H, 6.85%; N, 23.73% (VarioEL); calcd. for C 11 H 17 N 4 O 6 (336.74) -C, 55.92%; H, 6.83%; N, 23.71%. Experimental detailsAll the H atoms were treated as riding-model, with N-H = 0.86 Å, C-H = 0.93-0.98 Å, and their U iso = 1.2U eq (carrier atom). DiscussionThe aminoguanidine derivatives with aldehyde or keto group have been employed to prepare metal complexes for its biological activities in the research area of bioinorganic chemistry [1][2][3][4]. The title compound is a new aminoguanidine derivative and has been synthesized in a convenient approach in our work. It was expected to be used as a ligand to obtain vanadium complexes, which have the potential insulin-mimetic effect [5,6]. The title compound is a perchlorate salt, the structure of the cation moiety will be discussed in this work. The 1-(3,4-dimethoxy)phenyl-1-methane imino guanidine molecule was protonated to obtain the title salt. The bond length of C2-N4 is 1.291(3) Å, showing a double bond formed by the condensation of the ketone and amino groups. However, the bond distance of C1-N1 (1.309(3) Å) and C1-N2 (1.315(3) Å) are not significantly different, which may be considered that the two bonds were delocalized. The cation moieties were linked each to other form an infinite chain by the N-H×××O hydrogen bonds by the amino and methoxyl groups. The distances and angles of bond N2-H2A×××O5 and N2-H2A×××O6 were 2.975(3) Å, 2.989(3) Å and 107.5°, 130.0°, respectively. In the chain, the neighbouring cations were not coplanar, their intersection angle was 51°. Sequentially, perchlorate anions are connected to the infinite chains constructing a two-dimensional layer by the N-H×××O hydrogen bonds through the guandine groups and perchlorate anions. The distances and angles of bond N1-H1B×××O2, N2-H2B×××O1, and N3-H3×××O1 were 2.991(3) Å, 2.906(4) Å, 3.034(3) Å and 130.4°, 150.6°, 140.1°, respectively. Further, the weaker hydrogen bonds between the N1, N2 atoms of the guandine groups and O2, O1 atoms of the perchlorate anions enlarge the two-dimentional network into a three-dimentional network. The distances and angles of bond N1-H1A×××O2 and N2-H2A×××O1 were 3.105(4) Å, 3.161(4) Å and 165.5°, 144.5°, respectively.

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Synthesis, characterization and crystal structure of square-pyramidal copper(II) complexes with pyridoxylidene aminoguanidine

Cited by 21 publications

References 15 publications

Synthesis, characterization and thermal behavior of copper(II) complexes with pyridoxal thiosemi (PLTSC)- and S-methylisothiosemicarbazone (PLITSC)

Synthesis, characterization and thermal behavior of copper(II) complexes with pyridoxal thiosemi (PLTSC)- and S-methylisothiosemicarbazone (PLITSC)

Syntheses and characterization of 2-acetylpyridine-aminoguanidine and its copper(II) complexes: Crystallographic and antimicrobial study

Crystal structure of (E)-1-((1-(3,4-dimethoxyphenyl)ethyl)imino) guanidinium perchlorate, C11H17ClN4O6

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