JSCS Vol 80, No 7

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J. Serb. Chem. Soc. 80 (7) 839–852 (2015)

UDC 547.71.8+547.639.5+546.98+542.913:615.281/.282; JSCS–4763; doi: 10.2298/JSC150116013B; Original scientific paper

 

Synthesis and antimicrobial activity of azepine and thiepine derivatives

NINA BOŽINOVIĆ, IRENA NOVAKOVIĆ*, SLAĐANA KOSTIĆ RAJAČIĆ*, IGOR M. OPSENICA and BOGDAN A. ŠOLAJA

Faculty of Chemistry, University of Belgrade, Studentski trg 16, P. O. Box 51, 11158, Belgrade, Serbia

*Institute of Chemistry, Technology, and Metallurgy, University of Belgrade, Njegoševa 12, 11000 Belgrade, Serbia

 

(Received 16 January, revised 2 February, accepted 6 February 2015)

A series of new pyridobenzazepine and pyridobenzothiepine derivatives was synthesized by Pd-catalyzed formation of CN and CS bonds. All synthesized compounds were tested for their in vitro antimicrobial activity. The pyridobenzazepine derivatives showed better antibacterial and antifungal activity than the corresponding dipyridoazepine analogue. Among the synthesized azepines, derivative 8 displayed potent activity against the tested bacteria (MIC ranged 39–78 µg mL-1), while azepine 12 showed promising antifungal activity (MIC ranged 156–313 µg mL-1). The synthesized thiepine derivatives exhibited weak antibacterial activity, but showed pronounced antifungal activity.

 

Keywords: azepines; thiepines; heterocycles; palladium; antibacterials; antifungal.

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J. Serb. Chem. Soc. 80 (7) 853–866 (2015)

UDC 547.9+544.473:577.15+547.918+542.913+66.094.941; JSCS–4764; doi: 10.2298/JSC150914112W; Original scientific paper

 

Ultrafast synthesis of isoquercitrin by enzymatic hydrolysis of rutin in a continuous-flow microreactor

JUN WANG*,**, AN GONG**, SHUANGSHUANG GU**, HONGSHENG CUI** and XIANGYANG WU*

*School of Environment and Safety Engineering, Jiangsu University, Zhenjiang 212013,
P. R. China

**School of Biotechnology, Jiangsu University of Science and Technology, Zhenjiang 212018, P. R. China

 

(Received 15 September, revised 6 November, accepted 13 November 2014)

Isoquercitrin is a rare flavonol glycoside with a wide range of biological activities and is a key synthetic intermediate for the production of enzymatically modified isoquercitrin. In order to establish an ultrafast biopro-cess for obtaining isoquercitrin, a novel continuous flow biosynthesis of isoquercitrin using the hesperidinase-catalyzed hydrolysis of rutin in a glass–polydimethylsiloxane (PDMS) microreactor was first performed. Using the developed microchannel reactor (200 μm width, 50 μm depth and 2 m length) with one T-shaped inlet and one outlet, the maximum yield of isoquercitrin (98.6 %) was achieved in a short time (40 min) under the following optimum conditions: rutin concentration at 1 g L-1, hesperidinase concentration at 0.1 g mL-1, reaction temperature 40 °C, and a flow rate of 2 μL min-1. The value of the activation energy, Ea, of the enzymatic reaction was 4.61 kJ mol-1, and the reaction rate and volumetric productivity were approximately 16.1-fold and 30 % higher, respectively, than those in a batch reactor were. Thus, the use of a continuous-flow microreactor for the enzymatic hydrolysis of rutin is an efficient and simple approach to achieve a relatively high yield of isoquercitrin.

 

Keywords: biocatalysis; continuous flow; hesperidinase; isoquercitrin; microreactor.

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J. Serb. Chem. Soc. 80 (7) 867–875 (2015)

UDC 546.562+546.732:548.7+547.772+547.857.8; JSCS–4765; doi: 10.2298/JSC140722009J; Original scientific paper

 

Synthesis and crystal structure of Cu(II) and Co(II) complexes with the 1,3-dimethylpyrazole-5-carboxylic acid ligand

ŽELJKO K. JAĆIMOVIĆ, MILICA KOSOVIĆ, SLAĐANA B. NOVAKOVIĆ*, GERALD GIESTER** and ANA RADOVIĆ***

Faculty of Metallurgy and Technology, University of Montenegro, Podgorica, Montenegro

*Vinča Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, P. O. Box 522, 11001 Belgrade, Serbia

**Institut für Mineralogie und Kristallographie, Fakultät für Geowissenschaften, Geographie und Astronomie, University of Vienna, Althanstraße 14, A-1090 Vienna,, Austria

***Accreditation Body of Montenegro, Jovana Tomaševića 1, 81000 Podgorica, Montenegro

 

(Received 22 July, revised 30 December 2014, accepted 30 January 2015)

In the reaction of 1,3-dimethylpyrazole-5-carboxylic acid (HL) with M(OAc)2·4H2O, (M = Cu or Co), two novel complexes were prepared, the square-planar [CuL2(H2O)2] and the octahedral [CoL2(MeOH)4]. The crystal structures were determined by single-crystal X-ray diffraction. In both complexes, the deprotonated acid displays monodentate coordination to the metal ions. According to the results of a CSD survey, this is the first structural report on the metal complexes with an N1-substituted pyrazole-5-carboxylic ligand.

 

Keywords: pyrazole-based ligand; transition metal complex; crystal structure.

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J. Serb. Chem. Soc. 80 (7) 877–888 (2015)

UDC 547.514.72+546.732:547.521+519.677:544.112–185; JSCS–4766; doi: 10.2298/JSC141107025A; Original scientific paper

 

Nucleus-independent chemical shift profiles along the intrinsic distortion path for Jahn–Teller active molecules. Study on the cyclopentadienyl radical and cobaltocene

LJUBICA ANDJELKOVIĆ, MARKO PERIĆ, MATIJA ZLATAR and MAJA GRUDEN-PAVLOVIĆ*

Center for Chemistry, ICTM, University of Belgrade, Njegoševa 12, 11001 Belgrade, Serbia

*Faculty of Chemistry, University of Belgrade, Studentski Trg 12–16, 11001 Belgrade, Serbia

 

(Received 7 November 2014, revised 11 March, accepted 12 March 2015)

The aromatic/anti-aromatic behavior of the cyclopentadienyl anion (Cp-), bis(η5-cyclopentadienyl)iron(II) (Fe(Cp)2), as well as of the Jahn–Teller (JT) active cyclopentadienyl radical (Cp·) and bis(η5-cyclopentadienyl)cobalt(II) (Co(Cp)2) were investigated using density functional theory (DFT) calculations of the nuclear independent chemical shifts (NICS). According to the NICS values, pentagon ring in Fe(Cp)2 is more aromatic than that of the isolated Cp-. The NICS parameters were scanned along the Intrinsic Distortion Path (IDP) for Cp· and Co(Cp)2 showing anti-aromaticity, which decreased with increasing deviation from the high symmetry D5h to the low symmetry (LS) C2v. Changes in the NICS values along the IDP revealed that Co(Cp)2 in the LS nuclear arrangement has aromatic character, in contrast to the case of Cp·.

 

Keywords: vibronic coupling; DFT; aromaticity; metallocene.

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J. Serb. Chem. Soc. 80 (7) 889–902 (2015)

UDC 546.766+541.183+66.095.26+544.713.432; JSCS–4767; doi: 10.2298/JSC140701024H; Original scientific paper

 

The adsorption behavior and mechanistic investigation of Cr(VI) ions removal by poly(2-(dimethylamino)ethyl methacrylate)/poly(ethyleneimine) gels

ZHENGBO HOU, WEIXIA ZHU, HANG SONG, PENGFEI CHEN and SHUN YAO

School of Chemical Engineering, Sichuan University, Chengdu, 610065, China

 

(Received 14 July, revised 24 December 2014, accepted 4 March 2015)

The composite hydrogels based on 2-(dimethylamino)ethyl methacrylate (DMAEMA) and polyethyleneimine (PEI) were prepared by amino radical polymerization and confirmed by Fourier transform infrared (FTIR) spectroscopy and elemental analysis. Then adsorption behavior and mechanism of Cr(VI) ions adsorption on the obtained materials were investigated by scanning electron microscopy, zeta potential determination and thermogravimetric analysis, etc. The adsorption process was found to follow pseudo-second order kinetics and the Langmuir model, and the maximum adsorption capacity of Cr(VI) ions reached 122.8 mg g-1. X-ray photoelectron spectroscopy (XPS) and pH analysis revealed that the Cr(VI) ions were adsorbed into the gels through the electrostatic interaction mechanism, and SO42- in the solution had a great effect on the adsorption process. In addition, a high pH and ionic strength could reduce the uptakes of the adsorbate, which could be used for desorption of Cr(VI) ions from the gels.

 

Keywords: 2-(dimethylamino)ethyl methacrylate; polyethyleneimine; adsorption; Cr(VI); polymerization.

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J. Serb. Chem. Soc. 80 (7) 903–915 (2015)

UDC 543.637–035.67+667.281+546.133.1:66.099.72+541.135; JSCS–4768, doi: 10.2298/JSC140917107M; Original scientific paper

 

Electrochemical decolorization of the Reactive Orange 16 dye using a dimensionally stable Ti/PtOx anode

DUŠAN Ž. MIJIN, VUK D. TOMIĆ AND BRANIMIR N. GRGUR

Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11020 Belgrade, Serbia

 

(Received 17 September, revised 5 November, accepted 6 November 2014)

The electrochemical decolorization of Reactive Orange 16 in a chloride containing solution was studied using a dimensionally stable Ti/PtOx anode. Different reaction parameters, agitation speed, applied current, sodium chloride concentration, and dye concentration were varied and the optimum electrolysis conditions were suggested. Hypochlorous acid was suggested to be the active species in the electrochemical decolorization. Moreover, the reaction was studied using UV–Vis spectrophotometry, high-pressure liquid chromatography (HPLC), total organic carbon (TOC) and total nitrogen (TN) analyses.

 

Keywords: reactive dye; azo dye; electrolysis, hypochlorite; hypochlorous acid.

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J. Serb. Chem. Soc. 80 (7) 917–931 (2015)

UDC 678.652+542.913+547.462.3:544.351.3:66.095.26; JSCS–4769 doi:10.2298/JSC140719003Z; Original scientific paper

 

Chemical synthesis and characterization of highly soluble conducting polyaniline in mixtures of common solvents

HICHEM ZEGHIOUD, SAAD LAMOURI, ZITOUNI SAFIDINE and MOHAMMED BELBACHIR*

Laboratoire de Chimie Macromoléculaire, Ecole Militaire Polytechnique, BP 17, Bordj El Bahri, Alger, Algeria

*Laboratoire de Chimie des Polymères, Département de Chimie, Faculté des Sciences, Université d’Oran, BP 1524 El’Menouer Oran 31000, Algeria

 

(Received 19 July, revised 29 December 2014, accepted 8 January 2015)

This work presents the synthesis and characterization of soluble and conducting polyaniline–poly(itaconic acid) PANI–PIA according to a chemical polymerization route. This polymerization pathway leads to the formation of doped polyaniline salts, which are highly soluble in a number of mixtures between organic common polar solvents and water, the solubility reaches 4 mg mL-1. The effect of synthesis parameters, such as doping level, on the conductivity was investigated and a study of the solubility and other properties of the resulting PANI salts were also undertaken. The maximum of conductivity was found equal to 2.48×10-4 S cm-1 for fully protonated PANI-EB. In addition, the synthesized materials were characterized by various methods, i.e., viscosity measurements, XRD analysis and FTIR and UV–Vis spectroscopy. Finally, TGA was performed to obtain some information concerning the thermal behaviour of the materials.

 

Keywords: conducting polymer; PANI; itaconic acid; polymerization; solubility properties.

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J. Serb. Chem. Soc. 80 (7) 933–946 (2015)

UDC 547.421–036.7+547.42+544.032.4:532.13+532.14; JSCS–4770; doi: 10.2298/JSC141009005V; Original scientific paper

 

Experimental study of the thermodynamic and transport properties of binary mixtures of poly(ethylene glycol) diacrylate and alcohols at different temperatures

JELENA M. VUKSANOVIĆ, IVONA R. RADOVIĆ, SLOBODAN P. ŠERBANOVIĆ AND MIRJANA LJ. KIJEVČANIN

Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11120 Belgrade, Serbia

 

(Received 9 October 2014, revised 16 January, accepted 19 January 2015)

Experimental density r, refractive index nD and viscosity h data of three binary systems of poly(ethylene glycol) diacrylate (PEGDA) + ethanol, + 1-propanol and + 1-butanol were measured at eight temperatures from 288.15 to 323.15 K, with temperature step of 5 K, and at atmospheric pressure. The experimental data were correlated as a function of the PEGDA mole fraction and temperature. The densities and refractive indices of the investigated mixtures could be fitted well with exponential function vs. composition, including the temperature dependence of the parameters, while in the case of the viscosities, a polynomial function fits well the composition of the mixtures. In the case of the temperature correlation, all three properties (ρ, ln η and nD) exhibited linear trends. The viscosity modeling was performed using four models: the UNIFAC–VISCO, ASOG–VISCO, McAllister and the Teja–Rice models. For application of the UNIFAC–VISCO model, interaction parameters of following groups were determined: CH2=CH/CH3, CH2=CH/CH2, CH2=CH/OH, CH2=CH/CH2O and CH2=CH/COO. In addition, in the same way, the binary interaction parameters used in the ASOG–VISCO model of the following groups were determined: CH2=CH/CH2, CH2=CH/OH, CH2=CH/CH2O and CH2=CH/COO.

 

Keywords: density; viscosity; refractive index; new UNIFAC–VISCO parameters; new ASOG–VISCO parameters.

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J. Serb. Chem. Soc. 80 (7) 947–957 (2015)

UDC 546.722+66.094.3+544.4:628.112; JSCS–4771; doi: 10.2298/JSC140204089M; Original scientific paper

 

The effect of iron oxidation in the groundwater of the alluvial aquifer of the Velika Morava River, Serbia, on the clogging of water supply wells

BRANKICA MAJKIĆ-DURSUN*, ANĐELKA PETKOVIĆ AND MILAN DIMKIĆ

Jaroslav Černi Institute for the Development of Water Resources, Jaroslava Černog 80, Belgrade, Serbia

 

(Received 4 February, revised 27 June, accepted 3 September 2014)

The oxidation of iron(II) dissolved in groundwater and subsequent precipitation of the oxidation products on the screens and discharge pipes of water wells that tap shallow alluvial aquifers leads to the formation of well encrustations. The main goal of the presented research was to determine the reasons for the rapid clogging of water supply wells. In the particular case of the alluvial aquifer of the Velika Morava River, Serbia, the encrustations include mostly iron-(hydr)oxides (62.6 to 76.2 wt. %). Groundwater over-exploitation leads to the mixing of different geochemical zones and the formation of a redox front. During the two-year survey, the concentrations of the dissolved oxygen in the groundwater varied over a wide range from 0.1 to 7.1 mg L-1 as the result of unsuitable exploitation regime. The on site measured groundwater temperature, concentrations of dissolved oxygen and pH values, and the laboratory analysis of dissolved iron concentrations showed that iron precipitation was favorable under groundwater over-exploitation conditions.

 

Keywords: iron encrustations; groundwater over-exploitations; Trnovče; redox front formation.

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J. Serb. Chem. Soc. 80 (7) 959–969 (2015)

UDC Vol. 80::2015::85 Journal of the Serbian Chemical Society; JSCS–4772; doi: 10.2298/JSC150306036N; Letter to the Editor

 

LETTER TO THE EDITOR

A survey on publishing policies of the Journal of the Serbian Chemical Society – On the occasion of the 80th volume

OLGICA NEDIĆ and ALEKSANDAR DEKANSKI*

Institute for the Application of Nuclear Energy (INEP), University of Belgrade, Serbia

*Institute of Chemistry, Technology and Metallurgy, Department of Electrochemistry, University of Belgrade, Serbia

 

(Received 6 March, accepted 6 April 2015)

Journal of the Serbian Chemical Society (JSCS) is the scientific journal of the Serbian Chemical Society and this year is celebrating 85 years of its publishing and the 80th volume. After so many years of publishing, the idea of the Editorial Board of the JSCS was to investigate the opinion of the authors, reviewers and Sub-Editors concerning the journal and whether their evaluation and suggestions could aid in its improvement. Questionnaires were sent to the three investigated groups as an e-mail link. The responses were analyzed and only the most general and the most important data are presented in this article. The grades, comments and suggestions showed that most of the contributors are satisfied with the present handling and publishing policy of the JSCS, but certain technical aspects should be improved. After a thorough inspection of the data, the Editorial Board decided to introduce a fully automatic on-line system, to speed-up the peer review process, to improve the Instructions to Authors and Reviewer’s Report Form. All these novelties commenced from the beginning of March 2015.

 

Keywords: peer review; publishing; questionnaire; evaluation

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July 25. 2015.

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