Vol 80, No 8 - Abstracts

JSCS Vol 80, No 8

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J. Serb. Chem. Soc. J. Serb. Chem. Soc. 80 (8) 971–982 (2015)

UDC 546.831–31+546.723’+22+547.831:542.9+544.47:544.344; JSCS–4773; doi: 10.2298/JSC141023031H; Original scientific paper

Preparation and characterization of ZrO₂-supported Fe₃O₄-MNPs as an effective and reusable superparamagnetic catalyst for the Friedländer synthesis of quinoline derivatives

SEYYEDEH ZOHA HEJAZI, ABDOLLAH FALLAH SHOJAEI, KHALIL TABATABAEIAN and FARHAD SHIRINI

Department of Chemistry, Faculty of Sciences, University of Guilan, P. O. Box 41335-1914, Rasht, Iran

(Received 23 October 2014, revised 4 March, accepted 27 March 2015)

In this study, a convenient, appropriate and eco-friendly method for the synthesis of quinoline derivatives via a Friedländer reaction was developed using ZrO2/Fe3O4-MNPs as an effective and reusable heterogeneous catalyst. The morphology of ZrO2/Fe3O4-MNPs was studied by the XRD, FT-IR, SEM, TEM and VSM techniques. Green reactions, straight and easy work-up, high yields of the products and good reaction times are the benefits of this procedure. Further, the catalyst could be recovered using an external magnetic field and reused at least three times without a considerable decrease in its catalytic activity.

Keywords: quinoline derivatives; Friedländer reaction; ZrO2/Fe3O4-MNPs; heterogeneous catalyst; green procedure.

Full Article - PDF 332 kB Available OnLine: 13. 04. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 983–996 (2015)

UDC 637.12+66.061+547.584–326:543.544.3:543.51; JSCS–4774; doi: 10.2298/JSC141204028M; Original scientific paper

Evaluation of a method for phthalate extraction from milk related to the milk dilution ratio

DANICA S. MILOJKOVIĆ, DARKO H. ANĐELKOVIĆ, GORDANA M. KOCIĆ* and TATJANA D. ANĐELKOVIĆ

Faculty of Sciences and Mathematics, University of Niš, Višegradska 33, 18000 Niš, Serbi

*Faculty of Medicine, University of Niš, Bulevar dr Zorana Đinđića 81, 18000 Niš, Serbia

(Received 4 December 2014, revised 26 February, accepted 19 March 2015)

Liquid–liquid extraction techniques coupled with gas chromatography–mass spectrometry (GC–MS) were compared for the extraction and the determination of four phthalates: dimethyl phthalate (DMP), di-n-butyl phthalate (DBP), benzyl butyl phthalate (BBP) and di-(2-ethylhexyl) phthalate (DEHP) in six different kinds of milk-based samples. Extraction factors: sample preparation, organic solvent type and volume, salt effect, agitation and the extraction time were optimized. The ions of the base peak (m/z 149 for DBP, BBP and DEHP and m/z 163 for DMP) for the investigated phthalates were selected for the screening studies. The acquisition was performed in the selected ion-monitoring mode. The response of the mass selective detector (MSD) for GC–MS phthalate calibration standards was linear between 0.25 and 2.50 µg mL-1 with calculated limit of detection (LOD) values between 0.01 to 0.04 µg mL-1 and limit of quantitation (LOQ) values of 0.05 to 0.12 µg mL-1, while repeatability was between 1.7 to 4.9 % relative standard deviation (RSD). The study demonstrated an increase in the recovery of less polar phthalates in matrix milk standards on matrix dilution. Recovery for hydrophilic phthalates, such as DMP, was not changed by matrix dilution and it was continuously low for the investigated method. Two spiking levels, tested for the influence of matrix dilution on phthalate recovery, showed the same trend.

Keywords: extraction efficiency; phthalate esters; gas chromatography-mass spectrometry; milk samples.

Full Article - PDF 213 kB Supplementary Material PDF 143 kB Available OnLine: 27. 03. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 997–1008 (2015)

UDC 544.112+541.135+532.14:547.772+547.211+547.759.32+546.47:537.872; JSCS–4775; doi: 10.2298/JSC150224027Z; Original scientific paper

QTAIM investigation of a dipyrazol-1-ylmethane derivative and its Zn(II) complexes (ZnLX₂, X = Cl, Br or I)

MARYAM DEHESTANI and LEILA ZEIDABADINEJAD

Department of Chemistry, Shahid Bahonar University of Kerman, 76169 Kerman, Iran

(Received 24 February, revised 27 March, accepted 31 March 2015)

Topological analyses of the electron density were performed on the bis(pyrazol-1-yl)methane derivative 9-(4-(di-1H-pyrazol-1-ylmethyl)phenyl)-9H-carbazole (L) and its zinc(II) complexes: ZnLCl2 (1), ZnLBr2 (2) and ZnLI2 (3) using the quantum theory of atoms in molecules (QTAIM) at the B3PW91/6-31g(d) theoretical level. The topological parameters derived from the Bader theory were also analyzed; these are characteristics of Zn-bond critical points and of ring critical points. The calculated structural parameters were the frontier molecular orbital energies, the highest occupied molecular orbital energy (EHOMO), the lowest unoccupied molecular orbital energy (ELUMO), hardness (η), softness (S), the absolute electronegativity (χ), the electrophilicity index (ω) and the fractions of electrons transferred (ΔN) from ZnLX2 complexes to L. Numerous correlations and dependencies between the energy terms of the symmetry adapted perturbation theory approach (SAPT), geometrical, topological and energetic parameters were detected and are described.

Keywords: ZnLX2; charge transfer; bond critical point; SAPT

Full Article - PDF 427 kB Available OnLine: 13. 04. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 1009–1017 (2015)

UDC 539.6+544.131; JSCS–4776; doi: 10.2298/JSC150126015G; Original scientific paper

Multicenter Wiener indices and their applications

IVAN GUTMAN*,**, BORIS FURTULA* and XUELIANG LI***

*Faculty of Science, University of Kragujevac, P. O. Box 60, 34000 Kragujevac, Serbia

**State University of Novi Pazar, Novi Pazar, Serbia

***Center for Combinatorics, Nankai University, Tianjin, 300071, China

(Received 26 January, revised 12 February, accepted 13 February 2015)

The Wiener index W could be viewed as a molecular structure descriptor composed of increments representing interactions between pairs of atoms. A generalization of the W are the Steiner–Wiener indices W_k, k = 3, 4, … In the quantity, W_k interactions between k-tuples of atoms play a role, based on the concept of the Steiner distance. It is shown that the term W + lW_k provides an approximation for the boiling points of alkanes better than W itself. The best such approximation is obtained for k = 7.

Keywords: Wiener index; multicenter Wiener index; Steiner distance; Steiner–Wiener index; molecular graph.

Full Article - PDF 196 kB Available OnLine: 15. 02. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 1019–1034 (2015)

UDC 547.551.41+546.766+547.288.1+546.141:542.9:531.3; JSCS–4777; doi: 10.2298/JSC140916001S; Original scientific paper

Dynamics of cetyltrimethylammonium bromide-mediated reaction of phenylsulfinylacetic acid with Cr(VI): Treatment of pseudo-phase models

PERUMAL SUBRAMANIAM and NATESAN THAMIL SELVI*

Research Department of Chemistry, Aditanar College of Arts and Science, Tiruchendur-628 216, Tamil Nadu, India

*Govindammal Aditanar College for Women, Tiruchendur-628 215, Tamil Nadu, India

(Received 19 September, revised 28 December, accepted 31 December 2014)

The influence of cetyltrimethylammonium bromide, CTAB, on the oxidative decarboxylation of phenylsulfinylacetic acid, PSAA, and several meta- and para-substituted PSAAs by Cr(VI) was investigated in 95 % H2O–5 % CH3CN medium. The rate profile displayed a peculiar trend with an initial rate increase at low CTAB followed by sharp rate inhibition at higher CTAB concentrations. The initial rate acceleration could be explained by strong binding of SO42- on the positively charged micellar surface. The specific partitioning of PSAA in the micellar phase by hydrophobic interaction and the oxidizing species HCrO3+ in aqueous phase by electrostatic repulsion accounted for the rate retardation at higher CTAB concentrations. The Hammett plot with different substituted PSAAs showed excellent correlation affording negative ρ value, which supports the proposed mechanism involving the intermediate formation of sulfonium cation. The obtained ρ value in CTAB medium was found to be slightly lower than that in aqueous medium. Quantitative analysis of the rate data for the inhibition shown by CTAB was performed using the Menger–Portnoy and the Piszkiewicz pseudo-phase models. The binding constant for PSAA with micelles was evaluated from the Piszkiewicz cooperative model.

Keywords: phenylsulfinylacetic acid; Cr(VI); CTAB micellar effect; Hammett correlation; Piszkiewicz cooperative model.

Full Article - PDF 272 kB Available OnLine: 05. 01. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 1035–1049 (2015)

UDC 577.182.24+543.552+544.6.076.32–034.791:519.677; JSCS–4778, doi: 10.2298/JSC150129019N; Original scientific paper

Voltammetric and theoretical studies of the electrochemical behavior of cephalosporins at a mercury electrode

KATARINA NIKOLIĆ, MARA M. ALEKSIĆ, VERA KAPETANOVIĆ and DANICA AGBABA

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

(Received 29 January, revised 23 February, accepted 26 February 2015)

The adsorption and electroreduction behavior of cefpodoxime proxetil, cefotaxime, desacetylcefotaxime, cefetamet, ceftriaxone, ceftazidime, and cefuroxime axetil at a mercury electrode surface were studied using cyclic (CV), differential pulse (DPV) and adsorptive stripping differential pulse (AdSDPV) voltammetry. The quantitative structure property relationship (QSPR) study of the seven cephalosporins adsorption at the mercury electrode was based on density functional theory DFT-B3LYP/6-31G(d,p) calculations of molecular orbitals, partial charges and electron densities of the analytes. The DFT-parameters and QSPR model explain well the process of adsorption of the examined cephalosporins. The QSPR study defined that cephalosporins with lower electron density on the nitrogen atom of the N–O bond, higher number of hydrogen bond-accepting groups, and higher principal moment of inertia should express high adsorption on the mercury electrode.

Keywords: cephalosporins; AdSDPV; CV; DFT; QSPR; computational electrochemistry.

Full Article - PDF 315 kB Available OnLine: 18. 11. 2014. Cited by

J. Serb. Chem. Soc. 80 (8) 1051–1059 (2015)

UDC *Desmodium styracifolium:547.42/.43+577.152.1:541.18.043+541.18.045; JSCS–4779 doi:10.2298/JSC140919023L; Original scientific paper

Analysis of alcohol dehydrogenase inhibitors from Desmodium styracifolium using centrifugal ultrafiltration coupled with HPLC–MS

LIANGLIANG LIU*, MIAO CHEN* and XIAOQING CHEN*^,**

*Institute of Bast Fiber Crops, Chinese Academy of Agricultural Sciences, Changsha 410205, China

**School of Chemistry and Chemical Engineering, Central South University, Changsha 410083, China

(Received 19 September, revised 16 December 2014, accepted 9 March 2015)

Alcohol dehydrogenase (ADH) inhibitors play an important role in the treatment of human methanol or ethylene glycol poisoning and the suppression of acetaldehyde accumulation in alcoholics. In this study, centrifugal ultrafiltration coupled with high performance liquid chromatography-mass spectrometry (HPLC–MS) was utilized to screen and identify ADH inhibitors from an ethyl acetate extract of Desmodium styracifolium (Osb.) Merr. The experimental conditions of the centrifugal ultrafiltration were optimized. Under the optimum conditions (ADH concentration: 37.5 μg mL-1, incubation time: 90 min, pH 7.0 and temperature: 15 °C), formononetin and aromadendrin were successfully screened and identified from the ethyl acetate extract of D. styracifolium. The screening result was verified by ADH inhibition assays. The IC50 values of formononetin and aromadendrin were 70.8 and 84.7 μg mL-1, which were in accordance with their degrees of binding. Aromadendrin was for the first time reported to have inhibitory activity on ADH. This method provides an effective way to screen active compounds from natural products.

Keywords: alcohol dehydrogenases; aromadendrin; centrifugal ultrafiltration; Desmodium styracifolium; formononetin.

Full Article - PDF 215 kB Available OnLine: 16. 03. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 1061–1071 (2015)

UDC 678–13+533.583+544.773.42/.43+546–3:544.722.132; JSCS–4780; doi: 10.2298/JSC141014029K; Original scientific paper

Structural effects of the monomer type on the properties of copolyimides and copolyimide–silica hybrid materials

CANAN KIZILKAYA, MERVE BICEN, SEVIM KARATAS and ATILLA GUNGOR

Marmara University, Faculty of Science and Letters, Department of Chemistry, 34722, Istanbul, Turkey

(Received 14 October 2014, revised 26 February, accepted 19 March 2015)

In this work, the effects of two different diamine monomers containing phosphine oxide on the thermal, mechanical and morphological properties of copolyimides and their hybrid materials were investigated. The gas separation properties of the synthesized copolyimides were also analyzed. The two different diamine monomers containing phosphine oxide were bis(3-aminophenyl]phenylphosphine oxide (BAPPO) and bis[4-(3-aminophenoxy)phenyl)phenylphosphine oxide (m-BAPPO). In the synthesis of the copolyimides, 3,3′-diaminodiphenyl sulfone (3,3′-DDS) was also used as the diamine, as well as 2,2-bis(3,4-dicarboxyphenyl)hexafluoropropane dianhydride (6FDA). Copolyimide films were prepared by thermal imidization. Furthermore, hybrid materials containing 5 % SiO2 were synthesized by the sol–gel technique. Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance spectroscopy (NMR) confirmed the expected structures. Dynamic mechanical analysis (DMA) demonstrated that the m-BAPPO-based copolyimides had lower glass transition temperatures (Tg) than the BAPPO-based ones. The thermal decomposition temperature of the m-BAPPO-containing copolyimide without silica was shifted to a higher value. The moduli and strength values of the BAPPO diamine-containing copolyimide and its hybrid were higher than those of the m-BAPPO-containing materials. Contact angle measurements showed their hydrophobicity. Scanning electron microscope (SEM) analysis showed the dispersion of the silica particles in the copolyimides. These copolyimides may be used in the coating industry. The CO2 permeability and the permselectivity were the highest, among the other values found in this study, when the m-BAPPO-containing copolyimide in the absence of silica was used. The gas permeabilities obtained from this work were in the decreasing order: PCO2 > PO2 > PN2.

Keywords: copolyamic acid; inorganic compound; sol–gel; imidization; hydrophobic nature; permeation.

Full Article - PDF 177 kB Supplementary Material PDF 381 kB Available OnLine: 27. 03. 2015. Cited by

J. Serb. Chem. Soc. 80 (8) 1073–1085 (2015)

UDC 547.216+547.533+547.412.1:532.14+542.3:537.11; JSCS–4781; doi: 10.2298/JSC141127026I; Original scientific paper

An apparatus proposed for density measurements in compressed liquid regions at pressures of 0.1–60 MPa and temperatures of 288.15–413.15 K

GORICA R. IVANIŠ, ALEKSANDAR Ž. TASIĆ, IVONA R. RADOVIĆ, BOJAN D. DJORDJEVIĆ, SLOBODAN P. ŠERBANOVIĆ and MIRJANA Lj. KIJEVČANIN

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

(Received 27 November 2014, revised 16 March, accepted 17 March 2015)

In this work, an apparatus for density measurements in the compressed liquid regions is presented. This installation is based on the use of a DMA HP density measuring cell and a DMA 5000 densimeter (both instruments are products of Anton Paar, Gratz, Austria). Calibration of the DMA HP cell was performed by applying the classical method in which a vacuum, water and n-decane were recommended to be used as calibration fluids. To test the capabilities of the set-up, the densities of n-hexane, toluene and dichloromethane were measured in the temperature interval 288.15 to 413.15 K and the pressure range 0.1–60 MPa. The obtained results were compared with the corresponding values found in the literature. Depending on the literature selected for comparison (the temperature and pressure ranges available), the average absolute percentage deviations were for n-hexane, 0.03–0.10 %; for toluene, 0.04–0.08 % and for dichloromethane, 0.02–0.03 %. A deeper insight into the results of this work showed that most of them were in good agreement with the literature values; higher discrepancies were evidenced in the vicinity of the ends of the temperature and pressure ranges.

Keywords: high pressure; elevated temperature; density; n-hexane; toluene; dichloromethane.

Full Article - PDF 250 kB Supplementary Material PDF 74 kB Available OnLine: 18. 11. 2014. Cited by

J. Serb. Chem. Soc. 80 (8) 1087–1099 (2015)

UDC 550.4.001.5:504.3.054+627.8.034.7:546.47/49’56’815(497.11); JSCS–4782; doi: 10.2298/JSC170914108P; Letter to the Editor

Geochemical investigation as a tool in the determination of the potential hazard for soil contamination (Kremna Basin, Serbia)

TAMARA PERUNOVIĆ, KSENIJA STOJANOVIĆ, MILICA KAŠANIN-GRUBIN*, ALEKSANDRA ŠAJNOVIĆ*, VLADIMIR SIMIĆ**, BRANIMIR JOVANČIĆEVIĆ and ILIJA BRČESKI

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

*University of Belgrade, Center of Chemistry, ICTM, Njegoševa 12, 11000 Belgrade, Serbia

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

(Received 17 September, revised 31 October, accepted 6 November 2014)

The geochemical composition of the soils and underlying sediments in the Kremna Basin was investigated. The aim was to assess whether the observed heavy metal concentrations in the soil samples represent geogenic or anthropogenic contamination. The second objective was to show that geochemical data of underlying sediments should be used as a tool in the determination of the potential hazard for soil contamination. For this purpose, the contents of As, Cr, Cu, Hg, Ni, Pb and Zn of soil samples were compared with standard values, a reference soil sample and local background values of the underlying sediments. The soil samples were unpolluted regarding the contents of As, Hg, Pb and Zn. All samples had higher contents of Cr and Ni, whereas three samples had higher contents of Cu than the limit standard values. Geochemical parameters showed that the higher concentrations of Cr, Cu and Ni in the soils could be attributed to geogenic impact. This conclusion was supported by the Chemical Proxy of Alteration and Chemical Index of Weathering values, which indicated intense weathering of the sediments. The obtained results showed that the Kremna area is under slight to moderate hazard if a land use change would occur, and proved the importance of the geochemical composition of underlying sediments in the interpretation of heavy metal pollution.

Keywords: soils; sediments; geochemistry; heavy metals; pollution; weathering.

Full Article - PDF 148 kB Supplementary Material PDF 165 kB Available OnLine: 18. 11. 2014. Cited by

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