Vol 79, No 10 - Abstracts

JSCS Vol 79, No 10

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J. Serb. Chem. Soc. 79 (10) 1199–1204 (2014)

UDC 547.261+547.313.2+547.415.1:542.913:535.33.004.12; JSCS–4657; doi: 10.2298/JSC140212042M; Original scientific paper

Novel methylene bridged ethylenediAMine-type ligands: synthesis and spectral characterization

LJILJANA E. MIHAJLOVIĆ-LALIĆ, ALEKSANDAR SAVIĆ, GABRIJELA BRAĐAN, TIBOR J. SABO and SANJA GRGURIĆ-ŠIPKA#

Faculty of Chemistry, University of Belgrade, Studentski trg 12–16, 11000 Belgrade, Serbia

(Received 12 February, revised 11 April, accepted 11 April 2014)

The synthesis of two new organic compounds, diisobutyl- and diisopentyl (S,S)-a1,a3-bis(cyclohexylmethyl-1,3-imidazolidinediacetate is reported herein. The one-pot procedure was realized by the addition of the reducing agent and carbonyl compound into a methanolic solution of the parent compounds (isobutyl and isopentyl esters of (S,S)-a,a¢-(1,2-ethanediyldiimino)bis[cyclohexanepropanoic acid] in appropriate stoichiometric ratios. The compounds were fully characterized by infrared, ESI-MS, 1D (1H and 13C) and 2D (COSY, HSQC and HMBC) NMR spectroscopy and elemental analysis. The spectral data confirmed the presence of the –CH2– group introduced between the nitrogen atoms of the ethylenediAMine moiety, revealing a neutral form of the potential bidentate ligand.

Keywords: cyclohexyl derivatives; ethylenediAMine; AMine ligands; potential drugs.

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J. Serb. Chem. Soc. 79 (10) 1205–1212 (2014)

UDC 577.175.73+547.918+547.563.13’023+542.913+66.094.414+66.095.12:61(510); JSCS–4658; doi: 10.2298/JSC131011026L; Original scientific paper

Improved synthesis of gastrodin, a bioactive component of a traditional Chinese medicine

YU-WEN LI and CUI-LI MA*

School of Chemistry and Pharmacy, Qingdao Agricultural University, Qingdao 266109, China

*Affiliated Hospital, Qingdao Agricultural University, Qingdao 266109, China

(Received 11 October 2013, revised 23 March, accepted 24 March 2014)

Highly practical, four-step synthesis of gastrodin was developed using penta-O-acetyl-b-D-glucopyranose and p-cresol as glycosyl donor and glycosyl acceptor, respectively, in 58.1 % overall yield. As the initial step, the penta-O-acetyl-b-D-glucopyranose was treated with p-cresol in the presence of BF3·Et2O as catalyst to generate 4-methylphenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside in 76.3 % yield. Further, this product was subjected to radical bromination with N-bromosuccinimide (NBS) to provide 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside in 91 % yield. Subsequently, reaction of 4-(bromomethyl)phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside with a solution of acetone and saturated aqueous sodium bicarbonate led to 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside in 93 % yield. Finally, global deprotection of 4-(hydroxymethyl)phenyl 2,3,4,6-tetra-O-acetyl-b-D-glucopyranoside under Zemplen conditions furnished gastrodin in 90 % yield. Compared to the previously reported methods, this protocol has the advantages of operational simplicity, chromatography-free separation, high overall yield, inexpensive and common reagents as well as less waste pollutants, rendering it an alternative suitable for industrial production.

Keyword: gastrodin; glycosylation; penta-O-acetyl-b-D-glucopyranose; radical bromination.

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J. Serb. Chem. Soc. 79 (10) 1213–1222 (2014)

UDC 582.751.9:665.52/.54:635.074:633.8:57–188; JSCS–4659; doi: 10.2298/JSC140227037C; Original scientific paper

Chemical constituents and biological activities against Tribolium castaneum (Herbst) of the essential oil from Citrus wilsonii leaves

HAI PING CHEN*^,**, KAI YANG*, CHUN XUE YOU*, SHU SHAN DU*, QIAN CAI**, QING HE***, ZHU FENG GENG*** and ZHI WEI DENG***

*State Key Laboratory of Earth Surface Processes and Resource Ecology, Beijing Normal University, Haidian District, Beijing 100875, China

**College of Pharmacy, Liaoning University of Traditional Chinese Medicine, Dalian 116600, Liaoning, China

***Analytical and Testing Center, Beijing Normal University, Beijing 100875, China

(Received 27 February, revised 4 April, accepted 7 April 2014)

The essential oil obtained from Citrus wilsonii Tanaka leaves by hydrodistillation was investigated by GC and GC–MS. The main components of the essential oil were identified to be citronellol (16.94 %), neryl acetate (10.35 %), γ-terpinene (9.85 %), citronellal (9.36 %) and β-pinene (6.72 %). These four compounds, predicted with a bioactivity-test to be the active constituents, were isolated and identified. It was found that the essential oil of C. wilsonii leaves and the isolated compounds possessed fumigant and contact toxicity against Tribolium castaneum adults. The essential oil and γ-terpinene showed strong fumigant toxicity against T. castaneum (LC50 = 8.18 and 4.09 mg L-1, respectively). The repellency of the crude oil and the active compounds was also determined. Citronellol, neryl acetate and β-pinene were strongly repellent (100, 86 and 92 %, respectively, at 78.63 nL cm-2, after 2 h treatment) against T. castaneum. The essential oil and citronellol exhibited the sAMe level of repellency compared with the positive control, N,N-diethyl-meta-toluAMide (DEET, N,N-diethyl-3-methylbenzAMide). The results indicate that the essential oil of C. wilsonii leaves and its active compounds had the potential to be developed as natural fumigants, insecticides and repellents for the control of T. castaneum.

Keywords: fumigant toxicity; contact toxicity; repellency; neryl acetate;γ-terpinene.

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J. Serb. Chem. Soc. 79 (10) 1223–1234 (2014)

UDC 663.551.5:634.2+54.061:641.1:663.12; JSCS–4660; doi: 10.2298/JSC140218030D; Original scientific paper

Influence of yeast and nutrients on the quality of apricot brandy

IVAN UROŠEVIĆ, NINOSLAV NIKIĆEVIĆ, LJUBIŠA STANKOVIĆ, BOBAN ANĐELKOVIĆ*, TIJANA UROŠEVIĆ, GORDANA KRSTIĆ* AND VELE TEŠEVIĆ*

Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080 Zemun, Serbia

*Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia

(Received 25 January, revised 13 March, accepted 14 March 2014)

Five yeast strains Saccharomyces cerevisiae and S. bayanus (SB, Top Floral, Top 15, Aroma White and Red Fruit) and two nutrients, diAMmonium phosphate and Nutriferm Arom, were exAMined for their influence on young apricot brandies, with a special emphasis on the chemical, volatile and sensory characteristics. Analyses of the major and minor volatiles and sensory analysis of the apricot brandies showed important differences between the sAMples. The total sensory scores of the apricot brandies ranged between 16.88 for the control sAMple to 18.35 for the sAMple produced with the SB yeast strain and diAMmonium phosphate as nutrient. All the sAMples of apricot brandies fulfilled EU requirements as regards their content of methanol and other components, such as acetaldehyde, ethyl acetate, and higher alcohols.

Keywords: apricot brandy; yeast strain; nutrients; volatile compounds.

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J. Serb. Chem. Soc. 79 (10) 1235–1247 (2014)

UDC 546.562+541.121:536.7:576+615.9:616–006.04; JSCS–4661; doi: 10.2298/JSC140404044T; Original scientific paper

Correlations between the in vitro antiproliferative activity, structure and thermal stability of some macrocyclic dinuclear Cu(II) complexes

SLAĐANA B. TANASKOVIĆ, MIRJANA ANTONIJEVIĆ-NIKOLIĆ*, BERTA BARTA HOLLÓ**, BRANKA DRAŽIĆ, TATJANA STANOJKOVIĆ***, KATALIN MÉSZÁROS SZÉCSÉNYI** AND GORDANA VUČKOVIĆ****

Faculty of Pharmacy, University of Belgrade, Vojvode Stepe 450, 11000 Belgrade, Serbia

*Higher Technological School of Professional Studies 15000, Šabac, Serbia

**Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia

***Institute for Oncology and Radiology of Serbia, Pasterova 14, 11000 Belgrade, Serbia

****Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11158 Belgrade, Serbia

(Received 4 April, revised 15 April, accepted 15 April 2014)

Seven macrocyclic dinuclear Cu(II) complexes with tpmc = N,N',N",N'"-tetrakis(2-pyridylmethyl)-1,4,8,11-tetraazacyclotetradecane of coordination formulae [Cu2tpmc](ClO4)4 (1), [Cu2(X)tpmc](ClO4)3·nH2O, X= F-, n = 0 (2), X = Cl-, n = 1 (3), X = Br-, n = 0 (4), X= I-, n = 1 (5), X == NO2-, n = 0 (6), [Cu2(NCS)2tpmc](ClO4)2 (7) were evaluated for their cytotoxic activity against human cervix adenocarcinoma (HeLa), human melanoma (Fem-x) and human colon carcinoma (LS174) cell lines. The results were compared with the corresponding data for the cis-diAMminedichloridoplatinum(II) (CDDP) as referent cytostatic, as well as with the free ligands and the solvent dimethyl sulfoxide (DMSO) as controls. The complexes showed considerable antiproliferative effect, although significantly less than CDDP. The thermal decomposition pattern of the complexes was determined by simultaneous TG/DSC measurements. The thermal stability of the compounds 2–7 followed the trend of their antiproliferative activity against the HeLa cell line, as well as their corresponding stability constants. The highest thermal stability and cytotoxicity belonged to complex [Cu2tpmc](ClO4)4, with no anionic co-ligand. Complex [Cu2(NO2)tpmc](ClO4)3 exhibited a selective cytotoxicity against LS174 cells, at the level of the most active [Cu2tpmc](ClO4)4.

Keywords: copper(II)complexes; octaazAMacrocycle; antiproliferative activity; thermal analysis.

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J. Serb. Chem. Soc. 79 (10) 1249–1261 (2014)

UDC 628.3+66.081+547.564.3+666.32:66.017; JSCS–4662, doi: 10.2298/JSC140206043M; Original scientific paper

Sorption of different phenol derivatives on a functionalized macroporous nanocomposite of poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate) and acid modified bentonite

SANJA R. MARINOVIĆ, ALEKSANDRA D. MILUTINOVIĆ-NIKOLIĆ, ALEKSANDRA B. NASTASOVIĆ*, MARIJA J. ŽUNIĆ, ZORICA M. VUKOVIĆ, DUŠAN G. ANTONOVIĆ** and DUŠAN M. JOVANOVIĆ

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

*University of Belgrade - Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, Njegoševa 12, Belgrade

**University of Belgrade, Faculty of Technology and Metallurgy, Karnegijeva 4, Belgrade, Republic of Serbia

(Received 6 February, revised 11 April, accepted 14 April 2014)

Macroporous nanocomposite of poly(glycidyl methacrylate-co-ethylene glycol dimethacrylate) and acid modified bentonite was prepared by radical suspension copolymerization. Nanocomposite was functionalized with diethylenetriAMine (DETA), by ring-opening reaction of the pendant epoxy groups. Functionalization was performed in order to enable phenol derivatives sorption. This new, not sufficiently investigated material, with developed porous structure was denoted CP–SA–DETA. In this study, the influence of temperature on 4-nitrophenol (4NP) sorption on CP–SA–DETA was investigated. The chemisorption was estimated as dominant process since activation energy of sorption of 4NP of 54.8 kJ mol-1 was obtained. After determining the optimal sorption conditions for 4NP, the sorption of 2-nitrophenol (2NP) and 2-chloro-4-nitrophenol (2Cl4NP) on CP–SA–DETA was investigated with respect to pH, initial concentration and contact time. The 2NP sorption was seldom tested, while according to our knowledge, the 2Cl4NP sorption was not investigated. The isotherm data were best fitted with Langmuir model, while the sorption dynAMics obeyed the pseudo-second-order kinetic model for all derivatives.

Keywords: functionalized nanocomposite; wastewater sorbent; 4-nitrophenol; 2-nitrophenol; 2-chloro-4-nitrophenol.

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J. Serb. Chem. Soc. 79 (10) 1263–1277 (2014)

UDC 547.564.4+546.56+547.261+547.84:62.178.063:543.4/.5; JSCS–4663; doi:10.2298/JSC140129034S; Original scientific paper

Spectrophotometric and conductometric study of the complexation of N-salicylidene-2-AMinophenol with Cu²⁺in methanol + 1,4-dioxane binary solutions

RASHMIDIPTA BISWAS, DHIRAJ BRAHMAN and BISWAJIT SINHA

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

(Received 29 January, revised 26 March, accepted 1 April 2014)

The complexation reaction between N-salicylidene-2-AMinophenol, abbreviated as SAP, with the Cu2+ was studied in binary mixtures of methanol and 1,4-dioxane using conductometric and spectrophotometric methods at different temperatures. The stability constants (Kf) for the 1:1 complex, Cu2+–SAP, were calculated from computer fitting of the absorbance and molar conductance data against various mole ratios (cM:cL or cL:cM) in different binary solvent mixtures. A non-linear behaviour was observed for the variation of log Kf for the complex against the solvent composition. Various thermodynAMic parAMeters (ΔH, ΔS and ΔG) for the formation of the Cu2+–SAP complex were determined from the temperature dependence of the stability constants (Kf). The overall results showed that the complexation reaction is entropy driven and is affected by the nature and composition of the mixed solvents.

Keywords: N-salicylidene-2-AMinophenol; Cu2+; stability constants; binary mixtures; methanol; 1,4-dioxane.

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J. Serb. Chem. Soc. 79 (10) 1279–1293 (2014)

UDC 615.2clopidogrel+546.226+541.8–039.7+543.544.3+519.248; JSCS–4664; doi: 10.2298/JSC131120013P; Original scientific paper

Application of gas chromatography analysis to quality control of residual organic solvents in clopidogrel bisulfate

ALEKSANDAR D. PAVLOVIĆ, LJUBIŠA M. IGNJATOVIĆ, SAŠA Z. POPOV, ALEKSANDAR R. MLADENOVIĆ* and IGOR N. STANKOVIĆ**

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

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

**University of Novi Sad, Faculty of Sciences, Trg Dositeja Obradovića 3, Novi Sad, Serbia

(Received 20 November 2013, revised 4 February, accepted 23 February 2014)

A direct-injection, split-mode capillary gas chromatographic procedure with flAMe ionization detection was developed for the analysis of eight solvents used in the synthesis and purification of the anti-thrombotic drug clopidogrel bisulfate. The solvents analyzed were methanol, acetone, dichloromethane (DCM), 2-butanol, cyclohexane, toluene, acetic acid and N,N-dimethylformAMide (DMF). In addition, because of dehydration of 2-butanol during the drying process, significant AMounts of 2-butanol dehydration products (1-butene, cis- and trans-isomers of 2-butene, 2,2′-oxybis[butane] and 1-(1-methylpropoxy)butane) may be detected in clopidogrel bisulfate sAMples. The content of each of these volatile products can be evaluated using the sAMe gas-chromatographic method, with quantification based on the response factor established for the chromatographic peak of 2-butanol. Based on a large number of result sets, retrospectively, from many different batches analyzed, conclusions were made about process variations and reliability and a lack of consistency was identified in the quality of the active substance from a particular producer source. Multivariate analysis was used as the statistical technique to classify the sAMples. From the analyzed set of 11 solvents, 6 of them were preselected based upon their occurrence in the sAMples and both Principal Component Analysis (PCA) and Hierarchical Cluster Analysis (HCA) were performed.

Keywords: volatile impurities; validation; chemometrics; multivariate analysis; GC.

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J. Serb. Chem. Soc. 79 (10) 1295–1307 (2014)

UDC 678.82+661.183.8+678.046+665.93:678.017:539.12; JSCS–4665; doi: 10.2298/JSC140121035B; Original scientific paper

The effect of the size and shape of alumina nanofillers on the mechanical behavior of PMMA matrix composites

SOMAYA AHMED BEN HASAN, MARIJA M. DIMITRIJEVIĆ, ALEKSANDAR KOJOVIĆ, DUŠICA B. STOJANOVIĆ, KOSOVKA OBRADOVIĆ-ĐURIČIĆ*, RADMILA M. JANČIĆ HEINEMANN and RADOSLAV ALEKSIĆ

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

*University of Belgrade, Faculty of Stomatology, Dr Subotića 8, Belgrade, Serbia

(Received 21 January, revised 31 March, accepted 2 April 2014)

Composites with the addition of alumina nanofillers show improvement in mechanical properties.Poly(methyl methacrylate), PMMA, was used as a matrix and two different types of nanofillers having extremely different shapes were added into the matrix to form the composites. The reinforcements were based on alumina nanoparticles having either a spherical shape or whiskers with a length to diAMeter ratio of 100. The influence of the size and shape of the alumina fillers and the loading on the mechanical properties of the prepared composite were studied using nanoindentation measurements and dynAMic mechanical analysis. It was observed that both alumina whiskers and spherical alumina nanoparticles added in the PMMA matrix improved the mechanical properties of the composites, but the improvement was significantly higher with reinforcement by alumina whiskers. The concentration of the reinforcing spherical alumina nanoparticles and alumina whiskers in the PMMA matrix varied up to 5 wt. %. The best performance was obtained by the addition of 3 wt. % of alumina whiskers in the PMMA matrix in terms of the mechanical properties of the obtained composite.

Keywords: polymer composite; particle shape; nanoindentation; dynAMic mechanical analysis.

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J. Serb. Chem. Soc. 79 (10) 1309–1322 (2014)

UDC 628.316.12:546.175+549.67; JSCS–4666; doi: 10.2298/SC140116038P; Original scientific paper

Modification of natural clinoptilolite for nitrate removal from aqueous media

JELENA B. PAVLOVIĆ, JELENA K. MILENKOVIĆ and NEVENKA Z. RAJIĆ*

1Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

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

(Received 16 January, revised 7 April, accepted 9 April 2014)

Natural zeolitic tuff from the Zlatokop mine (Vranjska Banja deposit, Serbia) was investigated as the starting material to obtain a low cost adsorbent for the removal of nitrate from aqueous media. The tuff rich in zeolite, clinoptilolite, was modified with several oxides, iron(III), manganese(IV) and magnesium, by simple procedures in order to make the clinoptilolite surface accessible for binding nitrate ions. The obtained oxide-modified zeolite sAMples were characterized by scanning electron microscopy and energy dispersive X-ray analysis (SEM/EDS), powder X-ray diffraction (PXRD), infrared spectroscopy (FTIR) and by measurement of their specific surface area. The effects of the adsorbent dosage (0.5, 1.0, 1.5 and 2.0 g), temperature (25, 35 and 45 °C) and initial nitrate concentration (c0, 100, 200 and 300 mg dm-3) on the binding efficiency were also studied. For all adsorbents, the efficiency increased with temperature. The type of the oxide affected the adsorption mechanism. The Fe(III) oxide-modified zeolite exhibited the best binding ability. For this adsorbent, the adsorption kinetics were studied and it was found that they were best represented by the pseudo-second-order model.

Keywords: natural zeolite; clinoptilolite; oxide-modified zeolite; nitrate; adsorption.

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J. Serb. Chem. Soc. 79 (10) 1323–1334 (2014)

UDC 546.214+66–914:551.52:547.53+547.533+547.534.1/.2; JSCS–4667; doi: 10.2298/SC140126039S; Original scientific paper

Adaptive-network-based fuzzy inference system (ANFIS) model-based prediction of the surface ozone concentration

MARIJA SAVIĆ, IVAN MIHAJLOVIĆ, MILICA ARSIĆ and ŽIVAN ŽIVKOVIĆ

University of Belgrade, Technical Faculty in Bor, Management Department, Vojske Jugoslavije 12, 19210 Bor, Serbia

(Received 26 January, revised 8 April, accepted 9 April 2014)

This paper presents the results of modeling the tropospheric concentration of ozone in dependence on volatile organic compounds - VOCs (benzene, toluene, m- and p-xylene, o-xylene and ethylbenzene) and inorganic compounds – NOx (NO and NO2) CO, H2S, SO2, and particulate matter (PM10) in the AMbient air, in parallel with meteorological parAMeters, i.e., temperature, solar radiation, relative humidity, and wind speed and direction. The modeling was based on measured results obtained during the year 2009. The measurements were performed at the measuring station located within an agricultural area, near the city of Zrenjanin (Serbian Banat, Serbia). Statistical analysis of obtained data, based on bivariate correlation analysis, indicated that accurate modeling could not be performed using the linear statistics approach. Moreover, considering that almost all the input variables have wide ranges of relative change (ratio of variance compared to range), the nonlinear statistic analysis method based on only one rule describing the behavior of the input variable most certainly would not present sufficiently accurate results. For these reason, the employed modeling approach was based on Adaptive-Network-Based Fuzzy Inference System (ANFIS). The model obtained using the ANFIS methodology resulted in high accuracy, with a prediction potential of above 80 %, considering that obtained determination coefficient for the final model was R2 = 0.802.

Keywords: ANFIS; modeling; NOx; ozone; VOCs.

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J. Serb. Chem. Soc. 79 (10) 1335 (2014))

Erratum (printed version only)

Issue No. 8 (2014), Vol. 79:

– Back Cover, Contents, instead of J. Serb. Chem. Soc. Vol. 79, No. 7 (2014), should be: J. Serb. Chem. Soc. Vol. 79, No. 8 (2014).

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