JSCS Vol 79, No 2

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J. Serb. Chem. Soc. 79 (2) 115–123 (2014)

UDC 547.53.024+547.78+547–316:615.281/.282; JSCS–4569; doi: 10.2298/JSC130114078S; Original scientific paper

 

Synthesis and antimicrobial activity of some new N-(aryloxoalkyl)-5-arylidene-thiazolidine-2,4-diones

ANCA STANA, BRÎNDUŞA TIPERCIUC, MIHAELA DUMA*, ADRIAN PÎRNĂU**, PHILIPPE VERITÉ***4 and OVIDIU ONIGA

Department of Pharmaceutical Chemistry, “Iuliu Haţieganu” University of Medicine and Pharmacy, 12 Ion Creangă Street, 400010 Cluj Napoca, Romania

*State Veterinary Laboratory for Animal Health and Food Safety, 400572 Cluj-Napoca, Romania

**National Institute for Research and Development of Isotopic and Molecular Technologies, 400293 Cluj Napoca, Romania

***University of Medicine and Pharmacy Rouen, Faculty of Pharmacy, Department of Analytical Chemistry, 22 Boulevard GAMbetta, F-76183 Rouen Cedex, France

 

(Received 13 January, revised 2 July 2013)

A series of new 5-(2,6-dichlorobenzylidene)thiazolidine-2,4-dione and 5-(4-methoxybenzylidene)thiazolidine-2,4-dione derivatives (3a–h and 5a–h, respectively) were synthesized starting from 5-arylidenethiazolidine-2,4-dione and α-halo-ketones. The structural elucidation of the newly synthesized compounds was based on elemental analysis and spectroscopic data (MS, 1H-NMR and 13C-NMR). The synthesized compounds were screened in vitro for their antimicrobial activities against several pathogenic strains of GrAM-positive and GrAM-negative bacteria and one fungal strain (Candida albicans), as growth inhibition diAMeters. Some of the compounds displayed better inhibitory activities than that of the reference drug against the GrAM-positive Staphylococcus aureus, Bacillus cereus and Listeria monocytogenes bacterial strains, and showed good antifungal activity against C. albicans, while the antibacterial activity against the GrAM-negative Escherichia coli and Salmonella typhimurium bacterial strains was moderate.

 

Keywords: 5-arylidenethiazolidine-2,4-dione; α-haloketone; antibacterial; antifungal.

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J. Serb. Chem. Soc. 79 (2) 125–132 (2014)

UDC 547.759.32+547.233+547.251.1+542.913+543.42:615.281/.282; JSCS–4570; doi: 10.2298/JSC130123069S; Original scientific paper

 

Synthesis, characterization and biological evaluation of some newer carbazole derivatives

DIVYANSHU SHARMA, NITIN KUMAR and DEVENDER PATHAK

Rajiv Academy for Pharmacy, Delhi-Mathura Highway, Chhattikara, Mathura - 281001, India

 

(Received 23 January, revised 16 June 2013)

A series of novel 5-[(9H-carbazol-9-yl)methyl]-N-[(substituted phenyl)(piperazin-1-yl)methyl]-1,3,4-oxadiazol-2-AMines (4ao) derivatives was synthesized by starting with carbazole, which on reaction with ethyl chloroacetate yielded ethyl 2-(9H-carbazole-9-yl)acetate (1). Compound 1 on reaction with semicarbazide followed by cyclisation with sulphuric acid gave 5-((9H-carbazole-9-yl)-1,3,4-oxadiazol-2-AMine (3), which through Mannich reaction with piperazine and a variety of aromatic aldehydes in the presence of acetic acid yielded the titled compounds (4ao). The structures of compounds were characterized by UV, FT-IR, 1H-NMR and MS spectral studies, and by elemental analysis. All the derivatives were evaluated for their antibacterial, antifungal and anticancer activities. Among the tested compounds, 4a, 4d, 4e and 4n exhibited significant antibacterial and antifungal activity, while the compounds 4a, 4d, 4k and 4n were found to be active on the human breast cancer cell line MCF7.

 

Keywords: Mannich reaction; antibacterial activity; antifungal activity; MCF7; synthesis; spectroscopy.

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J. Serb. Chem. Soc. 79 (2) 133–150 (2014)

UDC 612.398+544.022:659.24:57; JSCS–4571; doi: 10.2298/JSC130716100I; Original scientific paper

 

A bioinformatics study concerning the structural and functional properties of human caveolin proteins

ADRIANA ISVORAN*,**, DANA CRACIUN***, ALECU CIORSAC****, NAHUEL PERROT*****, VERONICA BESWICK*****,****** PIERRE NEDELLEC*****, ALAIN SANSON*****and NADEGE JAMIN*****

*Department of Biology–Chemistry, West University of Timisoara, 16 Pestalozzi, 300316 Timisoara, Romania

**Laboratory of Advanced Researches in Environmental Protection, West University of Timisoara, 4 Oituz, 300086 Timisoara, Romania

***Teacher training Department, West University of Timisoara, 4 V. Pirvan, 300223 Timisoara, Romania

****Department of Physical Education and Sport, Politehnica University of Timisoara, 2 P-ta Victoriei, 300306 Timisoara, Romania

*****Commissariat à l’Energie Atomique (CEA), Institute of Biology and Technologies of Saclay (iBiTecS) 91191 Gif-sur-Yvette Cedex, France

******Department of Physics, Université d’Evry-val-d’Essonne, 91025 Evry Cedex, France

 

(Received 16 July, revised 21 September 2013)

A bioinformatics study was performed to predict and compare the structural and functional properties of human caveolins: caveolin-1, -2 and -3. The computed local physicochemical properties, predictions of their secondary structure elements and interacting partners of caveolin-2 and -3 were compared to the experimentally determined structural and functional properties of caveolin-1. These data combined with sequence alignments of the three caveolins allowed the functional domains of caveolin-2 and -3 to be predicted and characterised. The hydrophobic regions of these proteins are highly similar in sequences and physicochemical properties, which is in good agreement with their known membrane locations and functions. The most divergent in terms of sequences and properties are the C-terminal regions of the caveolins, suggesting that they might be responsible for their distinct predicted interactions, with direct consequences on signalling processes.

 

Keywords: secondary structure; disordered regions; functional domains.

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J. Serb. Chem. Soc. 79 (2) 151–165 (2014)

UDC 577.213.3+546.962+542.9+547.571+547.551:543.42–74; JSCS–4572; doi: 10.2298/JSC121201073S; Original scientific paper

 

Synthesis, spectral, DNA binding and cleavage properties of ruthenium(II) Schiff base complexes containing PPh3/AsPh3 as co-ligands

SUBBAIYAN SATHIYARAJ, GANESAN AYYANNAN and CHINNASAMY JAYABALAKRISHNAN

Post Graduate and Research Department of Chemistry, Sri RAMakrishna Mission Vidyalaya College of Arts and Science, Coimbatore – 641 020, TAMil Nadu, India

 

(Received 1 December 2012, revised 8 May 2013)

Dihydroxybenzaldehyde-based Schiff base ligands (L1–L3) and their ruthenium(II) complexes were synthesized and characterized by elemental analysis, 1H-, 13C- and 31P-NMR, UV–Vis, IR and mass spectroscopy. The DNA binding of the ruthenium(II) complexes was investigated by UV–Vis absorption spectroscopy. The experiments revealed that all the compounds could bind to DNA through electrostatic interactions and the intrinsic binding constants (Kb) were estimated under similar sets of experimental conditions. The absorption spectral study indicated that the ruthenium(II) complexes had intrinsic binding constants in the range of (1.6–8.6)×104 mol-1 dm3. The complex [Ru(CO)(PPh3)2(L3)] bound more strongly than the other complexes. In addition, the DNA cleavage properties for all ruthenium(II) complexes were tested.

 

Keywords: Schiff base; ruthenium(II) complexes; CT-DNA; nuclease activity.

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J. Serb. Chem. Soc. 79 (2) 167–173 (2014)

UDC 546.11’116’17:546.11’17’46:544.022:519.216 JSCS–4573; doi: 10.2298/JSC130412044X; Original scientific paper

 

Theoretical prediction on the structures of the HMgN and HNMg using multiconfigurational methods

CUI-PING XIAO, WEN-ZUO LI, QING-ZHONG LI and JIAN-BO CHENG

The Laboratory of Theoretical and Computational Chemistry, College of Chemistry and Chemical Engineering , Yantai University, Yantai 264005, China

 

(Received 12 April, revised 23 April 2013)

The nine-valence-electron HMgN- and HNMg- have been investigated for the first time theoretically using complete active space self-consistent field (CASSCF) and multiconfiguration second-order perturbation theory (CASPT2) methods in conjunction with the contracted atomic natural orbital (ANO) basis sets. The structures of the low-lying electronic states of HMgN- and HNMg- were predicted. The possible unimolecular conversions between HMgN- and HNMg- were discussed. The calculated results indicated that the ground-state of HMgN- is linear, while the ground-state HNMg- is bent, which is in contradiction to the Walsh rules, which predict linear structures for HXY systems containing 10 or fewer valence electrons.

 

Keywords: HMgN-; HNMg-; complete active space self-consistent field; multiconfiguration second-order perturbation theory.

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J. Serb. Chem. Soc. 79 (2) 175–183 (2014)

UDC 547.233–304.2+544.723.232:66.011:615; JSCS–4574; doi: 10.2298/JSC130208046O; Original scientific paper

 

Modeling of ligand binding to the dopAMine D2 receptor

LILIANA OSTOPOVICI-HALIP and RAMONA RAD-CURPAN

Romanian Academy, Institute of Chemistry Timişoara, Computational Chemistry Department, 24 Mihai Viteazul Av., 300223-Timişoara, Romania

 

(Received 8 February, revised 4 April 2013)

The dopAMinic receptors for a long time have been major targets for the development of new small molecules with high affinity and selectivity to treat psychiatric disorders, neurodegeneration, and drug abuse, and in other therapeutic areas. In the absence of a 3D structure for the human dopAMine D2 (HDD2) receptor, the efforts for the discovery and design of new potential drugs rely on comparative models generation, docking and pharmacophore development studies. To obtain a better understanding of the HDD2 receptor binding site and the ligand–receptor interactions, a homology model of the HDD2 receptor based on the X-ray structure of the β2-adrenergic receptor was built and used to dock a set of partial agonists of the HDD2 receptor. The main characteristics of the binding mode for the HDD2 partial agonists set are given by the particular folding of a ligand and a complex network of contacts represented by stacking interactions, salt bridge and hydrogen bond formation. The characterization of the binding mode of the partial agonists at the HDD2 receptor provides the information required to generate pharmacophore models, which represent essential information for future virtual screening studies in order to identify new potential HDD2 partial agonists.

 

Keywords: GPCR; homology modeling; D2 receptor; molecular docking.

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J. Serb. Chem. Soc. 79 (2) 185–198 (2014)

UDC 579.8:544.537:543.426.1; JSCS–4575; doi: 10.2298/JSC130417088M; Original scientific paper

 

Investigation and detection of cyanobacterial Cr-phycoerythrin by laser-based techniques

BRATISLAV P. MARINKOVIĆ, AMBRA DELNERI*, MAJA S. RABASOVIĆ, MIRA TERZIĆ**, MLADEN FRANKO* and DRAGUTIN ŠEVIĆ

Institute of Physics, Belgrade, P. O. Box 68, University of Belgrade, Serbia

*Laboratory for Environmental Research, University of Nova Gorica, Slovenia
**Faculty of Science, University of Novi Sad, Serbia

 

(Received 17 April 2013)

The application of the high-sensitivity method of time resolved laser induced fluorescence (TR-LIF) and a flow-injection system by thermal lens spectrometry (FIA-TLS) for the analysis of Cr-phycoerythrin (Cr-PE) isolated from a proprietary cyanobacterium is presented. In the excitation wavelength range (340–470 nm), the fluorescence spectra exhibited a pronounced maximum at 575 nm. Another maximum at about 600 nm could also be observed. The obtained results were used to verify the technical parAMeters of the employed thermal lens technique, which is complementary to spectrofluorimetry and subject to lower sensitivity in the case of high fluorescence quantum yields and photolability of the measured compounds.

 

Keywords: time resolved laser induced fluorescence spectroscopy; thermal lens spectroscopy; phycoerythrin; cyanobacteria.

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J. Serb. Chem. Soc. 79 (2) 199–209 (2014)

UDC 547.995.3+546.722’817+539.196+543.552+66.087; JSCS–4576; doi: 10.2298/JSC130219048N; Original scientific paper

 

A new electrochemical method for the determination of chondroitin sulfate based on its suprAMolecular interaction with the cupferron–lead(II) complex

XUELIANG NIU, PINGPING ZHANG, WEILI ZHANG and WEI SUN*3

Department of Pharmacy, Shangdong Wanjie Medical College, Zibo,255213, Chin and Key Laboratory of Biomedical Engineering and Technology in the Universities of Shandong (Shangdong Wanjie Medical College), 255213, China

*College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao,266042, China

 

In this paper, the interaction of cupferron (Cup) and its lead(II) complex [Cup–Pb(II)] with chondroitin sulfate (CS) was investigated by the linear sweep voltAMmetric method. In the selected medium of pH 5.5 (acetic acid–hexAMine buffer solution), Cup can interact with Pb(II) to form a stable complex of [Cup–Pb(II)], which has a sensitive second order derivative polarographic reductive peak at –0.64 V vs. SCE. After the addition of CS into a solution of the Cup–Pb(II) complex, the reductive peak current decreased without any shift of the peak potential and no new peak appeared, which indicated that a non-electroactive suprAMolecular complex of CS with [Cup–Pb(II)] was formed. The binding reaction conditions were carefully investigated. The interaction mechanism under the optimal conditions was discussed. The decrease of reductive peak current, Ip″, was directly proportional to the CS concentration, thus a new quantitative determination method for CS was established with the linear regression equation as ∆Ip″ / nA =36.97(c / mg L-1) + 12.45 (n = 10, γ = 0.995). The effects of other substances on the determination were carefully investigated and three synthetic sAMples were determined with satisfactory results. The binding constant (βs) and the binding number (m) of CS with [Cup–Pb(II)] complex were calculated from the voltAMmetric data with the results βs = 1.89×1010 and m ≈ 2.5.

 

Keywords: cupferron; lead(II); chondroitin sulfate; linear sweep voltAMmetry; interaction

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J. Serb. Chem. Soc. 79 (2) 211–224 (2014)

UDC 678.562+544.773432+661.717.53:535.65:543.57; JSCS–4577; doi: 10.2298/JSC130219047L; Original scientific paper

 

Preparation and properties of fast temperature-responsive soy protein/PNIPAAm IPN hydrogels

YONG LIU, YINGDE CUI*, GUOJIE WU* and MIAOCHAN LIAO**

School of Chemistry and Chemical Engineering, Zhaoqing University, Zhaoqing 526061, China

*Institute of Green Chemical Engineering, Zhongkai University of Agriculture and Engineering, Guangzhou 510225, China

**Department of Logistics Management, Zhaoqing University, Zhaoqing 526061, China

 

(Received 19 February, revised 25 April 2013)

The interpenetrating polymer network of fast temperature-responsive hydrogels based on soy protein and poly(N-isopropylacrylAMide) were successfully prepared using sodium bicarbonate (NaHCO3) solutions as the reaction medium. The structure and properties of the hydrogels were characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, differential scanning calorimetry and thermal gravimetric analysis. The swelling and deswelling kinetics were also investigated in detail. The results showed that the proposed hydrogels had a highly porous structure, good miscibility and thermal stability, and a fast temperature response. The presence of NaHCO3 had little effect on the volume phase transition temperature (VPTT) of the hydrogels, and the VPTTs were at about 32 °C. Compared with the traditional hydrogels, the proposed hydrogels had much faster swelling and deswelling rates. The swelling mechanism of the hydrogels was non-Fickian diffusion. These fast temperature-responsive hydrogels may have potential applications in the field of biomedical materials.

 

Keywords: soy protein; poly(N-isopropylacrylAMide); hydrogels; fast response.

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J. Serb. Chem. Soc. 79 (2) 225–239 (2014)

UDC 546.723+547.313.2’131+547.261–145.2:532.13; JSCS–4578; doi: 10.2298/JSC170413082B; Original scientific paper

 

Solution behaviour of (N,N′-ethylenebis(salicylideneiminato))iron(III) chloride in aqueous methanol at 298.15, 303.15 and 313.15 K

DHIRAJ BRAHMAN and BISWAJIT SINHA

Department of Chemistry, University of North Bengal, Darjeeling-734013, India

 

(Received 14 April, revised 19 July 2013)

In this study partial molar volumes  and viscosity B-coefficients of (N,N′-ethylene-bis(salicylideneiminato))iron(III) chloride, abbreviated as FeIII(salen)Cl, in different aqueous methanolic solutions were determined from solution density and viscosity measurements at the temperatures 298.15, 303.15, and 313.15 K under AMbient pressure. The apparent molar volumes (φV) and densities (ρ) were used to calculate the apparent molar expansibilities (φE), the partial molar expansibilities  and the temperature dependence of the partial molar expansibilities  at constant pressure,  of FeIII(salen)Cl solutions to reveal the nature of different interactions in the ternary solutions. The transition state theory was applied to analyze the viscosity B-coefficients based on the activation parAMeters of viscous flow. The overall results indicated strong solute–solvent interactions between FeIII(salen)Cl and the solvent molecules, preferentially with water molecules and that FeIII(salen)Cl acts as a net structure promoter in the ternary solutions. The UV–Vis absorption spectra of the ternary solutions stand in support of the obtained results.

Keywords: partial molar volumes; viscosity B-coefficients; (N,N′-ethylenebis(salicylideneiminato))iron(III) chloride; aqueous methanol.

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J. Serb. Chem. Soc. 79 (2) 241–251 (2014)

UDC 532.135:665.33+631.8.022.3:537.872; JSCS–4579; doi: 10.2298/JSC130129062B; Original scientific paper

 

Rheological behaviour of castor oil mixed with different pyromellitic esters

SORINA BORAN and ANDRA TAMAS

CAICON Department, Faculty of Industrial Chemistry and Environmental Engineering, "Politehnica" University of Timisoara, Vasile Parvan Blv. 6, RO-300223 Timisoara, Romania

 

(Received 29 January, revised 29 April 2013)

The paper presents the rheological behaviour study of castor oil mixed with different pyromellitic esters. The pyromellitic tetra-esters used were obtained through the esterification of pyromellitic anhydride with a special alcohol with a complex alkyl–aryl structure (2-phenoxy-ethanol) in conjunction with linear aliphatic alcohols with variable length (n-butanol, n-decanol). The influences of the structure and concentration of the pyromellitic esters as well as that of temperature, on the rheological behaviour were determined from the dependence between the shear stress τ and the shear rate. An analysis of the dependence between τ and demonstrated that the studied solutions exhibited Newtonian behaviour. The evolution of the viscosity of the sAMples with temperature was characterized by Arrhenius type equations, the values of activation energy of viscous flow, Ea, were established. This constant can be correlated with the effect of friction reduction in the presence of additives. Characterization of the annulus of fluids flow under the effect of rotational motion was also realized by the calculation of the values of the Taylor–
–Reynolds number (Ta
Re).

 

Keywords: flow activation energy; Newtonian behaviour; oil additives; viscosity.

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J. Serb. Chem. Soc. 79 (2) 253–263 (2014)

UDC 666.32–039.7+661.183:628.193+620.266.1; JSCS–4580; doi: 10.2298/JSC130125065J; Original scientific paper

 

Organobentonites as multifunctional adsorbents of organic and inorganic water pollutants

NАТАŠA JOVIĆ-JOVIČIĆ, ALEKSANDRA MILUTINOVIĆ-NIKOLIĆ, MARIJA ŽUNIĆ, ZORICA MOJOVIĆ, PREDRAG BANKOVIĆ, BILJANA DOJČINOVIĆ*, ANA IVANOVIĆ-ŠAŠIĆ and DUŠAN JOVANOVIĆ

University of Belgrade, Institute of Chemistry, Technology and Metallurgy, Center for Catalysis and Chemical Engineering, Njegoševa 12, 11000 Belgrade, Serbia

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

 

(Received 13 January, revised 12 June 2013)

The aim of this study was to find a low cost, easy to synthesize and efficient adsorbent for the simultaneous adsorption of both organic and inorganic pollutants (including textile dyes, toxic metals, etc.). The starting material, domestic bentonite clay from Bogovina, was modified with AMounts of hexadecyltrimethylAMmonium cations corresponding to 0.5 and 1.0 times the value of the cation exchange capacity. The organobentonites were tested as adsorbents in a three-dye-containing solution, a three-component solution of Pb2+, Cd2+ and Ni2+ and a hexa-component solution containing all the investigated dyes and toxic metal cations. The used adsorbents showed the highest affinity toward acid yellow 99 and Ni2+. Dye adsorption was enhanced in the presence of toxic metal cations, while the adsorption of all toxic cations from the hexa-component solution was lower than from the three-component solution containing only toxic cations. The synthesized hexadecyltrimethylAMmonium bentonite could be regarded as an efficient multifunctional adsorbent for the investigated types of water pollutants.

 

Keywords: simultaneous adsorption; multi-component solutions; dyes; toxic metals; adsorption affinity.

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 J. Serb. Chem. Soc. 79 (2) 265–276 (2014)

UDC 546.3+66–914+551.578.4+625.712.2:551.321.7(497.113); JSCS–4581; doi: 10.2298/JSC130311052M; Original scientific paper

 

Multivariate analysis of the contents of metals in urban snow near traffic lanes in Novi Sad, Serbia

ALEKSANDRA MIHAILOVIĆ, MILICA VUČINIĆ VASIĆ, JORDANA NINKOV*, SUZANA ERIĆ**, NEBOJŠA M. RALEVIĆ, TOMAS NEMEŠ and ALEKSANDAR ANTIĆ

Faculty of Technical Sciences, University of Novi Sad, Trg Dositeja Obradovića 6, 21000 Novi Sad, Serbia

*Institute of Field and Vegetable Crops, Maksima Gorkog 30, 21000, Novi Sad, Serbia

**Faculty of Mining and Geology, University of Belgrade, Đušina 7, 11000 Belgrade, Serbia

 

(Received 11 March, revised 13 May 2013)

Abstract: During December 2009, snow was collected at twenty two locations across the urban area of Novi Sad, directly from roads and from traffic islands near crossroads. The total metal concentration was determined for each of ten metals (Al, Ca, Cu, Fe, K, Mn, Na, Ni, Pb and Zn) using the ICP-OES analytical technique. Ni was found to have the lowest concentration (0.0265 mg dm-3). Na was the metal with the highest concentration (10786 mg dm-3), which was the consequence of sodium chloride being used as a de-icing salt on the roads. The metal with the second highest concentration at all locations was Ca; this was most likely the result of soil dust. The Spearman rank correlation coefficients between analyzed metals were calculated to determine how the concentrations of the metals were related. Cluster analysis was performed on the obtained data sets, using both the hierarchical and partitioning methods in order to identify associations AMong metals and/or locations. It was shown that traffic density was not the most important factor that caused the differences between the concentrations of the metals in the sAMples.

 

Keywords: metal concentration; snow; traffic; correlation; cluster analysis.

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February 24. 2014.

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