JSCS Vol 79, No 3

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J. Serb. Chem. Soc. 79 (3) 277–282 (2014)

UDC 542.913:547.53.024’861.3+547.532’78:615.281/.282; JSCS–4582; doi: 10.2298/JSC130418058V; Original scientific paper

 

Synthesis and biological evaluation of 5-substituted derivatives of benzimidazole

VESNA P. VASIĆ, JELENA Z. PENJIŠEVIĆ, IRENA T. NOVAKOVIĆ, VLADIMIR V. ŠUKALOVIĆ, DEANA B. ANDRIĆ and SLAĐANA V. KOSTIĆ-RAJAČIĆ

Faculty of Chemistry, University of Belgrade, Studentski trg 12–16, Belgrade, Serbia

*ICTM – Center of Chemistry, University of Belgrade, Njegoševa 12, Belgrade, Serbia

 

(Received 18 April, revised 22 May 2013)

A series of eight novel 5-substituted derivatives of benzimidazole was synthesized by condensation of the corresponding diAMine with ethyl 4-[4-(2-chlorophenyl)piperazin-1-yl]butanoate in refluxing 4 M hydrochloric acid. In vitro antibacterial activity against ten strains, nAMely Bacillus subtilis, Clostridium sporogenes, Streptosporangium longisporum, Micrococcus flavus, Sarcina lutea, Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa, Salmonella enteritidis and Proteus vulgaris and antifungal activity against two fungal strains, nAMely Candida albicans and Saccharomyces cerevisiae, were evaluated. Of all the compounds screened for activity, 2-{3-[4-(2-chlorophenyl)piperazin-1-yl]propyl}-5-iodo-1H-benzimidazole and 2-{3-[4-(2-chlorophenyl)piperazin-1-yl]propyl}-5-methyl-1H-benzimidazole were associated with higher antifungal activity than commercial drugs.

 

Keywords: arylpiperazines; benzimidazoles; antibacterial activity; antifungal activity.

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J. Serb. Chem. Soc. 79 (3) 283–289 (2014)

UDC 547.495.2+547.496.3+542.913:57:615.27; JSCS–4583; doi: 10.2298/JSC120716095K; Original scientific paper

 

Synthesis and biological evaluation of novel urea and thiourea derivatives of valaciclovir

VENKATA RAMANA KATLA, RASHEED SYED, MADHAVA GOLLA, ADAM SHAIK* and NAGA RAJU CHAMARTHI

Department of Chemistry, Sri Venkateswara University, Tirupati - 517 502, India

*Department of Biochemistry, Sree Vidyaniketan P.G College, Tirupati - 517 502, India

 

(Received 12 July, revised 4 September 2012)

Series of novel urea and thiourea derivatives of valaciclovir were efficiently synthesized in high yields and their antiviral activity was evaluated. (S)-2-[(2-AMino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl 2-AMino-3-methylbutanoate (valaciclovir) (1) was reacted with various aromatic isocyanates/thiocyanates 2aj in the presence of N,N¢-dimethyl piperazine as a base in THF:pyridine (4:1) to obtain the valaciclovir urea/thiourea derivatives 3aj. The structures of the title compounds (3aj) were confirmed by their IR, NMR (1H and 13C) mass spectral data and elemental analysis. The newly synthesized compounds were screened for their antiviral activity against Tobacco mosaic virus (TMV) and antioxidant activity was evaluated by the 1,1-diphenyl-2-picrylhydrazyl radical (DPPH) and superoxide dismutase (SOD) scavenging methods. The title compounds exhibited potent antiviral and good antioxidant activities.

 

Keywords: isocyanate; isothiocyanate; N,N¢-dimethylpiperazine; tobacco mosaic virus; antiviral activity; antioxidant activity.

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J. Serb. Chem. Soc. 79 (3) 291–302 (2014)

UDC 542.9+546.562’141:547.759.32:548.7:543.57; JSCS–4584; doi: 10.2298/JSC130622084L; Original scientific paper

 

Transition metal complexes with thiosemicarbazide-based ligands. Part 60. Reactions of copper(II) bromide with pyridoxal S-methylisothiosemicarbazone (PLITSC). Crystal structure of [Cu(PLITSC–H)H2O]Br·H2O

VUKADIN M. LEOVAC, LJILJANA S. VOJINOVIĆ-JEŠIĆ, SONJA A. IVKOVIĆ*, MARKO V. RODIĆ, LJILJANA S. JOVANOVIĆ, BERTA HOLLÓ and KATALIN MÉSZÁROS SZÉCSÉNYI

Faculty of Sciences, University of Novi Sad, Trg D. Obradovića 3, 21000 Novi Sad, Serbia

*Faculty of Environmental Protection, University EDUCONS, V. Putnika bb, 21208 Sremska KAMenica, Serbia

 

(Received 22 June, revised 20 August 2013)

The synthesis and structural characterization of a square-planar copper(II) complex with pyridoxal S-methylisothiosemicarbazone (PLITSC) of the formula [Cu(PLITSC–H)H2O]Br·H2O (1) as the first Cu(II) complex with a monoanionic form of this ligand were described. Complex 1 together with two previously synthesized complexes [Cu(PLITSC)Br2] (2) and [Cu(PLITSC)-Br(MeOH)]Br (3) were characterized by elemental analysis, IR and electronic spectroscopy and by the methods of thermal analysis, conductometry and magnetochemistry.

 

Keywords: copper(II) complexes; pyridoxal S-methylisothiosemicarbazone; crystal structure; spectra; thermal analysis.

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J. Serb. Chem. Soc. 79 (3) 303–311 (2014)

UDC 547.789.1+547.594.3:546.3–386:535.33; JSCS–4585; doi: 10.2298/JSC121227042U; Original scientific paper

 

Heteroarylazo derivatives of cyclohexane-1,3-dione and their metal complexes

MUHAMMED BASHEER UMMATHUR, DAMODARAN KAMALAKSHY BABU* and KRISHNANNAIR KRISHNANKUTTY**

PG Department of Chemistry, KAHM Unity Women’s College, Manjeri, Kerala-676122, India

*Department of Chemistry, ZAMorin’s Guruvayurappan College, Calicut, Kerala-673014, India

**Department of Chemistry, University of Calicut, Kerala-673635, India

 

(Received 27 December 2012, revised 19 April 2013)

The coupling of diazotized 2-AMinothiazole and 2-AMinobenzothiazole with cyclohexane-1,3-dione yielded a new type of tridentate ligand system (HL). Analytical, IR, 1H-NMR, 13C-NMR and mass spectral data indicate the existence of the compounds in the intrAMolecularly hydrogen bonded azo–enol tautomeric form. Monobasic tridentate coordination of the compounds in their [CuL(OAc)] and [ML2] complexes [M = Ni(II) and Zn(II)] was established based on the analytical and spectral data. The Zn(II) chelates are diAMagnetic while the Cu(II) and Ni(II) complexes showed a normal parAMagnetic moment.

 

Keywords: heteroarylazo derivatives; 2-AMinothiazole; 2-AMinobenzothiazole; cyclohexane-1,3-dione; metal complexes; spectral data.

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J. Serb. Chem. Soc. 79 (3) 313–324 (2014)

UDC 661.34+546.34:541.18.045:543.51; JSCS–4586; doi: 10.2298/JSC130627083D; Original scientific paper

 

Study of the vaporization of LiI, LiI/C70, LiI/LiF/C70 from a Knudsen cell located in the ionization chAMber of a mass spectrometer

JASMINA ĐUSTEBEK, MIOMIR VELJKOVIĆ and SUZANA VELIČKOVIĆ

Vinča Institute of Nuclear Sciences, University of Belgrade, P. O. Box 522, 11001 Belgrade, Serbia

 

(Received 27 June 2012, revised 25 July 2013)

The vaporization of LiI, LiI/C70 and LiI/LIF/C70 was studied using a Knudsen cell located in the ionization chAMber of a magnetic sector mass spectrometer in the temperature range from 350 °C to 850 °C. The ion species, LinI+ (n = 2, 3, 4 or 6) were identified from the mixture LiI/C70, while the clusters LinI+ and LinF+ (n = 2, 3, 4, 5 or 6) were detected from a mixture LiI/LiF/C70. The intensities of LinI+ were higher than the emission of LinF+ cluster when the ratio of LiI to LiF was 2:1. By contrast, the emission of LinF+ is favored when the ratio of LiI to LiF was 1:2. These results show that the vaporization of a mixture LiI/LIF/C70 from a Knudsen cell located in the ionization chAMber of a mass spectrometer represents an efficient and simple way to obtain and investigate clusters of the type LinX, X = F or I. In this work, it was also shown that the trends of the In (Intensity, arb. units) versus temperature for all LinI+ clusters below and above the melting point of LiI were not sAMe. This suggested that the manner of formation of these clusters could be different due to changes in temperature.

 

Keywords: “superalkali” species; LinI clusters; LinF clusters.

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J. Serb. Chem. Soc. 79 (3) 325–330 (2014)

UDC 537.872:544.478–44+544.032.1:621.397.3; JSCS–4587; doi: 10.2298/JSC131002106Z; Extended abstract

 

EXTENDED ABSTRACT

Impact of the spatial distribution of morphological patterns on the efficiency of electrocatalytic gas evolving reactions

ALEKSANDAR R. ŽERAĐANIN

Department of Interface Chemistry and Surface Engineering, Max-Planck-Institut für Eisenforschung, Max-Planck-Straße 1, 40237 Düsseldorf, Germany

 

(Received 1 October 2013)

The efficiency of electrocatalytic gas evolving reactions (hydrogen, chlorine and oxygen evolution) is a key challenge for important industrial processes, such as chlor-alkali electrolysis or water electrolysis. The central issue for the aforementioned electrocatalytic processes is their huge power consumption. Experimental results accumulated in the past, as well as some predictive models (“volcano” plots) indicate that altering the nature of the electrode material cannot significantly increase the activity of the mentioned reactions. Consequently, it is necessary to find a qualitatively different strategy for improving the energy efficiency of electrocatalytic gas evolving reactions. A usually disregarded fact is that gas evolution is an oscillatory phenomenon. Given the oscillatory behavior, a key parAMeter of macrokinetics of gas electrode is the frequency of gas-bubble detachment. Bearing in mind that gas evolution greatly depends on the surface morphology, a methodology is proposed that establishes a rational link between the morphological pattern of an electrode with its activity and stability. Characterization was performed using advanced analytical tools. The frequency of gas-bubble detachment was obtained in the configuration of scanning electrochemical microscopy (SECM), while the corrosion stability was analyzed using a miniaturized scanning flow electrochemical cell connected to a mass spectrometer (SFC–ICPMS).

 

Keywords: energy efficiency; electrocatalysis; morphology; SECM; activity; stability.

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J. Serb. Chem. Soc. 79 (3) 331–340 (2014)

UDC 678.023.3+541.44’131:543.42–74:543.2; JSCS–4588; doi: 10.2298/JSC010413080M; Original scientific paper

 

The application of NIR spectroscopy with chemometric analysis for monitoring a powder blending process

LJILJANA B. MARIĆ, BRANISLAV D. JOVIĆ*, SLOBODAN D. PETROVIĆ**, ALEKSANDAR M. NIKOLIĆ* AND IRENA J. HOMŠEK

Galenika ad, Batajnički drum bb, 11080 Belgrade, Serbia

*Faculty of Sciences, University of Novi Sad, 21000 Novi Sad, Serbia

**Faculty of Technology and Metallurgy, University of Belgrade, 11000 Belgrade, Serbia

 

(Received 1 April, revised 14 July 2013)

Abstract: This paper reports the use of near infrared (NIR) spectroscopy as a process analytical technology (PAT) tool for monitoring the metformin (N,N-dimethylimidodicarbonimidic diAMide) hydrochloride and poly(vinyl pyrrolidone) (PVP) mixing process, which is the first stage in tablet production. Blend homogeneity was tested using the non-invasive NIR spectroscopy method and the partial least squares (PLS) regression model was applied for the analysis of the obtained spectra. Simultaneously, the critical parAMeter (metformin hydrochloride content) was monitored by a classical analytical technique, the validated HPLC method, commonly used for this purpose. Based on the high sensitivity of the model developed in this study, as well as the established correlation AMong the results obtained by different methods, it could be concluded that the proposed rapid and non-invasive technique could be an effecttive tool for the monitoring of one of the critical manufacturing steps in the production solid dosage forms.

 

Keywords: PAT; NIR spectroscopy; PLS; metformin hydrochloride; blend uniformity analysis.

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J. Serb. Chem. Soc. 79 (3) 341–344 (2014)

UDC 66.021.2.063.8+532.13+547.1:53.072; JSCS–4589; doi: 10.2298/JSC130610114K; Note

 

NOTE

Liquid mixture viscosities correlation with rational models

ANĐELA B. KNEŽEVIĆ-STEVANOVIĆ, GORAN M. BABIĆ*, MIRJANA Lj. KIJEVČANIN*, SLOBODAN P. ŠERBANOVIĆ* and DUŠAN K. GROZDANIĆ*

Metro Vancouver, 4330 Kingsway, Burnaby, British Columbia, V5H 4G8, Canada

*Chemical Engineering Department, Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

 

(Received 10 June, revised 27 August 2013)

In this paper, twenty two selected rational correlation models for the viscosities of liquid mixtures of organic compounds were tested on 219 binary sets of experimental data taken from the literature. The binary sets contained 3675 experimental data points for 70 different compounds. The Dimitrov–
–KAMenski X, Dimitrov–KAMenski XII, and Dimitrov–KAMenski XIII models demonstrated the best correlative characteristics for binary mixtures with an overall absolute average deviation of less than 2 %.

 

Keywords: binary mixture; liquid mixture viscosity; rational correlation models.

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J. Serb. Chem. Soc. 79 (3) 345–359 (2014)

UDC 546.42’226+546.42’264+547.288.1:661.566.097.3:544.4; JSCS–4590; doi: 10.2298/JSC130307066Z; Original scientific paper

 

Kinetics of conversion of celestite to strontium carbonate in solutions containing carbonate, bicarbonate and AMmonium ions, and dissolved AMmonia

MERT ZORAGA and CEM KAHRUMAN

Istanbul University, Engineering Faculty, Metallurgical and Materials Engineering Department, 34320, Avcilar, Istanbul, Turkey

 

(Received 7 March, revised 21 May 2013)

Celestite concentrate (SrSO4) was converted to SrCO3 in solutions containing CO32-, HCO3- and NH4+ and dissolved AMmonia. The effects of stirring speed, CO32- concentration; temperature and particle size of SrSO4 on the reaction rate were investigated. It was found that the conversion of SrSO4 was increased by increasing the temperature and decreasing the particle size, while the reaction rate was decreased with increasing the CO32- concentration. However, the stirring speed had no effect on the reaction rate. The conversion reaction was under chemical reaction control and the shrinking core model was suitable to explain the reaction kinetics. The apparent activation energy for the conversion reaction was found to be 41.9 kJ mol-1. The AMounts of the elements in the reaction solution were determined quantitatively by inductively coupled plasma-optical emission spectrometry. The characterization of the solid reactant and product was made using the scanning electron microscopy-energy dispersive spectrometry and X-ray powder diffraction analytical techniques.

 

Keywords: celestite; strontium sulfate; strontium carbonate; conversion; kinetics.

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J. Serb. Chem. Soc. 79 (3) 361–377 (2014)

UDC 628.3+535.6–26:544.4:66.011:66.099.72; JSCS–4591; doi: 10.2298/JSC130225075X; Original scientific paper

 

Kinetics and optimization of the decoloration of dyeing wastewater by a schorl-catalyzed Fenton-like reaction

HUAN-YAN XU, WEI-CHAO LIU, SHU-YAN QI, YAN LI, YUAN ZHAO and JI-WEI LI

School of Material Science and Engineering, Harbin University of Science and Technology, Harbin, 150040, P. R. China

 

(Received 25 February, revised 17 June 2013)

The kinetics and optimization of the decoloration of an active commercial dye, argazol blue BFBR (ABB), by a heterogeneous Fenton-like reaction catalyzed by natural schorl were investigated in this study. The kinetic investigations revealed that the first-order kinetic model was more favorable to describe the decoloration of ABB under different reaction conditions than the second-order and Behnajady–Modirshahla–Ghanbery models. The relationship between the reaction rate constant k and reaction temperature T followed the Arrhenius Equation, with an apparent activation energy Ea of 51.31 kJ·mol-1. The central composite design under the response surface methodology was employed for the experimental design and optimization of the ABB decoloration process. The significance of a second order polynomial model for predicting the optimal values of ABB decoloration was evaluated by the analysis of variance and 3D response surface plots for the interactions between the two variables were constructed. Then, the optimum conditions were determined.

 

Keywords: schorl; heterogeneous catalysis; argazol blue BFBR; response surface methodology; first-order kinetics.

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J. Serb. Chem. Soc. 79 (3) 379–387 (2014)

UDC 54.56’47’815’48:556.531:66.067.9(497.11)(282.243.743); JSCS–4592; doi: 10.2298/JSC130128085V; Original scientific paper

 

SHORT COMMUNICATION

Transport and storage of heavy metals in the Sava River Basin in Serbia

DUBRAVKA VUKOVIĆ, SRBOLJUB J. STANKOVIĆ*, ŽIVORAD VUKOVIĆ* AND KSENIJA JANKOVIĆ**

Institute of Veterinary Medicine, Vojvode Toze 24, 11000 Belgrade, Serbia

*Institute of Nuclear Sciences Vinča, University of Belgrade, P. O. Box 502, 11001 Belgrade, Serbia

**Institute for Testing Materials – IMS, Bulevar Vojvode Mišića 43, 11000 Belgrade, Serbia

 

(Received 28 January, revised 21 August 2013)

Selected heavy metals (Cu, Zn, Pb and Cd) in the water and sediment of the Sava River in Serbia were investigated from three locations in the vicinity of industrial and urban settlements (Šabac, Obrenovac and Belgrade) during the period spring 2007 to autumn 2011. The fluxes of heavy metals from the river water to the sediment due to sedimentation and heavy metal re-suspension fluxes arising from sediment re-suspension at high flows were determined, by application of a model for the assessment of the transport the pollutants through rivers. These fluxes were attributed mainly to natural processes.

 

Keywords: flux of heavy metal; river sediment; sediment re-suspension.

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