Vol 78, No 5 - Abstracts

JSCS Vol 78, No. 5

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J. Serb. Chem. Soc. 78 (5) 611–619 (2013)

UDC 547.821+547.759.32+542.913+547.631.1.05:66.095.253.095.252; JSCS–4442; doi: 10.2298/JSC120520098A Original scientific paper

Modern Friedel–Crafts chemistry. Part 36. Facile synthesis of some new pyrido[3,2,1-jk]carbazoles via Friedel–Crafts cyclialkylations

HASSAN ABDOU KOTB ABD EL-AAL and ALI ALI KHALAF

Chemistry Department, Faculty of Science, Assiut University, Assiut, 71516, Egypt

(Received 20 May 2011, revised 8 July 2012)

An efficient methodology for the synthesis of novel substituted pyrido[3,2,1-jk]carbazoles via Friedel–Crafts cyclialkylations is reported. The methodology was realized by a three-step protocol involving the addition of carbazole to 3-methylcrotononitrile. The resulting nitrile was subjected to alcoholysis to the desired ester, followed by addition of Grignard reagents to afford tertiary alcohols and/or reacted directly with different Grignard reagents to form the desired ketones. The latter ketones were converted to both secondary and tertiary alcohols by reduction with lithium aluminum hydride (LAH) and addition of Grignard reagents, respectively. These alcohols were cyclialkylated under Friedel–Crafts conditions catalyzed by AlCl3/CH3NO2, p-toluenesulfonic acid (PTSA) or polyphosphoric acid (PPA) to give tri- and tetra-substituted pyrido[3,2,1-jk]carbazoles.

Keywords: Friedel–Crafts cyclialkylation; pyrido[3,2,1-jk]carbazole; heteropolycycles; heteroarylalkanols; carbocations.

Full Article - PDF 206 KB Supplementary Material PDF 161 KB Available OnLine: 25.09. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 621–625 (2013)

UDC 547.551.42+547.831+547.554+542.913; JSCS–4443; doi: 10.2298/JSC120617081M Short communication

SHORT COMMUNICATION

Synthesis of quinolone substituted 2-azetidinone derivatives

UDAY C. MASHELKAR, MUKESH S. JHA and BEENA U. MASHELKAR

Organic Research Laboratory, S. S. and L. S. Patkar College, Goregaon (West), Mumbai 400 062, India

(Received 17 June, revised 30 July 2012)

Acetanilide was converted into 2-chloro-3-formylquinoline by reaction with DMF–POCl3 at 80–90 °C and then condensed with aromatic primary AMines to give Schiff bases 3a–c. These Schiff bases were then reacted with acid chlorides in toluene in the presence of a base to give 1,3,4-trisubstituted-2-azetidinones.

Keywords: acetanilide; 2-chloro-3-formylquinoline; aromatic AMine; acid chloride; tributylAMine; 2-azetidinone.

Full Article - PDF 190 KB Supplementary Material PDF 138 KB Available OnLine: 06.08. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 627–637 (2013)

UDC 547.783+66.081.2:544.351.3:615; JSCS–4444; doi: 10.2298/JSC120719118H Original scientific paper

Solvent effects on the absorption spectra of potentially pharmacologically active 5-alkyl-5-arylhydantoins: a structure–property relationship study

SLEEM F. HMUDA, NEBOJŠA R. BANJAC, NEMANJA P. TRIŠOVIĆ, BOJAN Đ. BOŽIĆ, NATAŠA V. VALENTIĆ and GORDANA S. UŠĆUMLIĆ

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

(Received 19 July, revised 22 October 2012)

To obtain insight into the interactions of potential anticonvulsant drugs with their surroundings, two series of 5-methyl-5-aryl- and 5-ethyl-5-arylhydantoins were synthesized and their absorption spectra were recorded in the region from 200 to 400 nm in a set of selected solvents. The effects of solvent dipolarity/polarizability and solvent–solute hydrogen bonding interactions on the absorption maxima shifts were analyzed by means of the linear solvation energy relationship (LSER) concept of KAMlet and Taft. The ratio of the contributions of specific and non-specific solvent–solute interactions were correlated with the corresponding absorption, distribution, metabolism, and excretion (ADME) properties of the studied compounds. The correlation equations were combined with different physicochemical parAMeters to generate new equations, which demonstrate the reasonable relationships between the solvent–solute interactions and the structure–activity parAMeters.

Keywords: hydantoin derivatives; KAMlet–Taft Equation; human intestinal absorption; lipophilicity, binding affinity.

Full Article - PDF 228 KB Supplementary Material PDF 147 KB Available OnLine: 06.11. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 639–651 (2013)

UDC *Pseudomonas aeruginosa:577.115+546.766+66.091.8+66–914.4; JSCS–4445; doi: 10.2298/JSC120831115A Original scientific paper

Influence of rhAMnolipids, produced by Pseudomonas aeruginosa NCAIM(P), B001380 on their Cr(VI) removal
capacity in liquid medium

NATAŠA S. AVRAMOVIĆ, SNEŽANA D. NIKOLIĆ-MANDIĆ* and IVANKA M. KARADŽIĆ*

School of Medicine, Department of Chemistry, University of Belgrade, Višegradska 26, Belgrade, Serbia
*Faculty of Chemistry, University of Belgrade, Studentski trg 12–16, Belgrade, Serbia

(Received 31 August, revised 29 October 2012)

Pseudomonas aeruginosa NCAIM(P), B001380, a propitious bacterial strain isolated from mineral cutting oil, was identified to be chromium tolerant and a producer of the biosurfactant rhAMnolipid (RL) with potential application in heavy metal bioremediation. Culture growth, RL production and Cr(VI) removal capacity of the strain in the presence of 50 mg L-1 Cr(VI) (I) and 100 mg L-1 Cr(VI) (II) were studied. The maximums of RL production were found in the late-stationary phase at 72 h for both Cr(VI)-AMended cultures: I (236 mg L-1) and II (160 mg L-1), as well as the maximums of the Cr(VI) removal capacity: 70 % (I) and 57 % (II). The AMount of Cr in RL preparation II was 22 mg mg-1, determined by flAMe atomic absorption spectroscopy (FAAS). Appearance of a new band at 914 cm-1 in infrared (IR) spectrum of RL (II) indicated significant proof for a possible coordination of CrO42- with RL. The effect of Cr(VI) on monorhAMnolipids (RL1) and dirhAMnolipids (RL2) distribution and their ratio were studied by electrospray ionization mass spectrometry (ESI-MS). An increase was observed in the RL2/RL1 ratio for II compared to the control.

Keywords: rhAMnolipids; chromium(VI); Pseudomonas; bioremediation.

Full Article - PDF 315 KB Available OnLine: 31. 10. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 653–667 (2013)

UDC 537.31–032.61+544.275–128:519.6:544.032.4; JSCS–4446; doi: 10.2298/JSC120307063C; Original scientific paper

Prediction of the electric conductivity of ionic liquids by two chemometrics methods

YU CAO, JIA YU, HANG SONG, XIANLONG WANG* and SHUN YAO

Department of Pharmaceutical and Biological Engineering, Sichuan University, Chengdu 610065, China

*School of Life Science and Technology, University of Electronic Science and Technology of China, Chengdu 610054, China and Department of Chemistry, Bryn Mawr College, 101 N Merion Ave, Bryn Mawr, PA 19010, USA

(Received 7 March, revised 12 June 2012)

In recent years, the study of the properties of ionic liquids (ILs) and their structures has developed largely. Among the common physicochemical properties of pure ILs, electric conductivity (EC) is of crucial importance for both practical and fundAMental viewpoint. In order to develop effective models for predicting the EC value of various ILs, the relationship between the structural descriptors and the EC of thirty-five ionic liquids at different temperatures was investigated by multi-linear regression (MLR) and a back propagation artificial neural network (ANN). As a result, a three layer ANN with four variables selected by the MLR model as input nodes was successfully set up. The descriptors selected by MLR were suitable and significant to be the input nodes of the ANN model in this study. Moreover, the ionic conductivities calculated by the ANN model, having a high correlation coefficient and low root mean squared error, were quantitatively in good agreement with the experimental values. The ANN model was proved to be better than the MLR model.

Keywords: electroconductibility; ionic liquids; multi-linear regression; artificial neural network.

Full Article - PDF 400 KB Available OnLine: 19.06. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 669–680 (2013)

UDC 547.922+547.53:532.783:547.565.2; JSCS–4447; doi: 10.2298/JSC120810114H; Original scientific paper

New cholesteryl-containing bent core liquid crystals

COSMIN-CONSTANTIN HUZUM, IRINA CARLESCU, GABRIELA LISA and DAN SCUTARU

Faculty of Chemical Engineering and Environmental Protection, Gheorghe Asachi Technical University of Iasi, 71 D. Mangeron St., 700050 – Iasi, Romania

(Received 10 August, revised 3 September 2012)

The paper presents the synthesis and mesomorphic behavior of two new series of bent core liquid crystalline compounds based on a 1,3-dihydroxybezene core and containing a cholesteryl 6-oxyhexanoate wing. The two series were obtained by esterification of the cholesteryl 6-(3-hydroxyphenoxy)hexanoate core with some 4-{[4-(n-alkyloxy)phenyl]azo}benzoic acids (n-alkyl = n-hexyl – n-dodecyl) or 4-{[4-(n-alkyloxy)benzoyl]oxy}benzoic acids (n-alkyl = n-hexyl – n-decyl). The esterification reactions were performed via the corresponding acyl chlorides or with the dicyclohexylcarbodiimide/4-(N,N-dimethylAMino)pyridine (DCC/DMAP) system. All the synthesized compounds evidenced enantiotropic liquid crystalline properties with smectic type textures when investigated by differential scanning calorimetry and polarized optical microscopy. Isotropization and isotropic to liquid crystal transitions occurred at relatively low temperatures (between 89 and 146 °C). The compounds containing the azo-aromatic linking group presented the largest range of stability of the mesophases (between 42 and 87 °C). All the investigated compounds were thermally stable in the range of the existence of mesophases.

Keywords: liquid crystals; banana shaped; cholesterol; resorcinol.

Full Article - PDF 418 KB Supplementary Material PDF 153 KB Available OnLine: 22. 10. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 681–688 (2013)

UDC 544.431.133:546.33’137:54–71:547.544; JSCS–4448; doi: 10.2298/JSC120706110F; Original scientific paper

Ionic strength effect on the deprotonation of para-sulfonatocalix[4]arene

MOHAMMAD FARAJI, ALI FARAJTABAR* and FARROKH GHARIB**

Department of Chemistry, IslAMic Azad University, Babol branch, Babol, Iran

*Department of Chemistry, IslAMic Azad University, Jouybar branch, Jouybar, Iran

**Chemistry Department, Faculty of Sciences, Shahid Beheshti University, Tehran, Evin, Iran

(Received 6 July 2012)

The deprotonation of para-sulfonatocalix[4]arene was studied by a combination of spectrophotometric and potentiometric methods at 25 °C. The ionic strength of the solutions was kept constant by sodium perchlorate as a background electrolyte at 0.10–4.0 mol dm-3. The spectral changes evidenced proton dissociation of only one hydroxyl group of calixarene in the studied pH range of 2–10. The pKa values were calculated using the STAR progrAM by multivariate curve resolution of the absorbance data. The results indicated that the acid–base behavior of para-sulfonatocalix[4]arene varied strongly with increasing ionic strength of the solution. The dependence of the deprotonation constant on ionic strength was explained by means of the Specific Ion Interaction Theory (SIT). The activity coefficients of the species were modeled using a modified SIT approach. The extracted specific ion interaction parAMeters were associated with the thermodynAMic deprotonation constant of para-sulfonatocalix[4]arene.

Keywords: deprotonation; sulfonatocalix[4]arene; ionic strength; SIT.

Full Article - PDF 218 KB Available OnLine: 22. 10. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 689–700 (2013)

UDC 54.74’77–31+544.6.076.324.4:541.135:544.35:544.654; JSCS–4449; doi: 10.2298/JSC120831112J; Original scientific paper

Ni–MoO₂ composite cathodes for hydrogen evolution in alkaline solution. Effect of aging of the electrolyte for their electrodeposition

VLADIMIR D. JOVIĆ, UROŠ Č. LAČNJEVAC, BORKA M. JOVIĆ, LJILJANA M. GAJIĆ-KRSTAJIĆ* and NEDELJKO V. KRSTAJIĆ**

Institute for Multidisciplinary Research, University of Belgrade, 11030 Belgrade, P. O. Box 33, Serbia

*Institute of Technical Sciences SASA, Knez Mihajlova 35, 11000 Belgrade, Serbia

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

(Received 31 August, revised 17 September 2012)

In this work, the effect of aging of the electrolyte in the electrodeposition of Ni–MoO2 composite coatings on their morphology (scanning electron microscopy), chemical composition (energy-dispersive X-ray spectroscopy), polarization characteristics and “service life”, tested for the hydrogen evolution reaction (HER) in 32 mass % NaOH at 90 °C, was investigated. Polarization characteristics and results of the “service life” test of Ni–MoO2 composite coatings obtained after different aging periods of the electrolyte for deposition (suspension of MoO2 powder particles in a solution containing 2 M NH4Cl + 0.2 M NiCl2) were compared with that recorded for the commercial De Nora’s Ni+RuO2 cathode coating (DN). It was shown that aging of the electrolyte did not influence the morphology and chemical composition of Ni–MoO2 composite coatings electrodeposited under conditions simulating their industrial production, while the polarization characteristics for the HER were influenced. The best coating, obtained after 180 days of electrolyte aging, showed a completely different (layered) structure of the deposit and significantly better performance than the commercial DN electrode during the “service life” test.

Keywords: Ni–MoO2 composite coating; hydrogen evolution; “service life” test.

Full Article - PDF 533 KB Available OnLine: 22. 10. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 701–711 (2013)

UDC 546.98+539.12:546.215:544.6.076.33–033.5–039.26+543.55; JSCS–4450; doi: 10.2298/JSC120619122K; Original scientific paper

Electrochemical determination of hydrogen peroxide at a glassy carbon electrode modified with palladium nanoparticles

SHIMELES ADDISU KITTE, BIRHANU DESALEGN ASSRESAHEGN and TESFAYE REFERA SORETA

Department of Chemistry, College of Natural Sciences, Jimma University, Ethiopia

(Received 19 June, revised 3. November 2012)

Herein the modifications of a glassy carbon electrode (GCE) with palladium nanoparticles and a palladium film are reported. The response to hydrogen peroxide on the modified electrode was exAMined using cyclic voltAMmetry and AMperometry (at –0.2 V vs. Ag/AgCl reference electrode in the phosphate buffer solution, pH 7.4). The palladium film and palladium nanoparticle-modified GCE showed a linear response to hydrogen peroxide in the concentration range 10 µM to 14 mM and 1 µM to 14 mM with detection limit of 6.79 and 0.33 µM, respectively.

Keywords: palladium; nanoparticles; hydrogen peroxide; glassy carbon electrode.

Full Article - PDF 196 KB Available OnLine: 14. 11. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 713–716 (2013)

UDC 66.094.3–541.135+533.9+661.8:667.62:669–034.7; JSCS–4451; doi: 10.2298/JSC121126129S; Extended abstract

EXTENDED ABSTRACT

Plasma electrolytic oxidation of metals

STEVAN STOJADINOVIĆ

University of Belgrade, Faculty of Physics, Studentski trg 12, 11000 Belgrade, Serbia

(Received 26 November 2012)

The results of investigation of the plasma electrolytic oxidation (PEO) process on some metals (aluminum, titanium, tantalum, magnesium and zirconium) were presented. The whole process involves anodizing metals above the dielectric breakdown voltage, when numerous micro-discharges are generated continuously over the coating surface. For characterization of the PEO process, optical emission spectroscopy and real-time imaging were used. These investigations enabled the determination of electron temperature, electron number density, spatial density of micro-discharges, the active surface covered by micro-discharges, and the dimensional distribution of the micro-discharges at various stages of the PEO process. Special attention was focused on the results of a study of the morphology, and the chemical and phase composition of oxide layers obtained in the PEO process on aluminum, tantalum and titanium in electrolytes containing tungsten. Physicochemical methods: atomic force microscopy (AFM), scanning electron microscopy (SEM-EDS), X-ray diffraction (XRD) analysis, X-ray photoelectron spectroscopy (XPS) and RAMan spectroscopy served as tools for exAMining the obtained oxide coatings. In addition, the application of the obtained oxide coatings, especially the application of TiO2/WO3 coatings, in photocatalysis was discussed.

Keywords: plasma electrolytic oxidation; micro-arc oxidation; micro-discharges; oxide coatings; optical emission spectroscopy.

Full Article - PDF 150 KB Available OnLine: 03. 12. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 717–724 (2013)

UDC 628.161.2:546.732+543.552+547.565.3:544.653.3; JSCS–4452; doi: 10.2298/JSC120305070H; Original scientific paper

Trace and selective determination of cobalt(II) in water and salt sAMples using cathodic adsorptive stripping voltAMmetry in the presence of Pyrogallol Red

FOROOZAN HASANPOUR, HOSSEIN TEIMORI*, MASOUD FOULADGAR** and MASOUMEH TAEI

Chemistry Department, PayAMe Noor University, 19395-4697 Tehran, Iran

*Cellular and Molecular Research Center, School of Medicine, Shahrekord University of Medical Sciences, Shahrekord, Iran

**Department of Biochemistry, Falavarjan Branch, IslAMic Azad University, Falavarjan, Iran

(Received 5 March, revised 16 June 2012)

A sensitive and selective procedure is presented for the voltAMmetric determination of cobalt. The procedure involves an adsorptive accumulation of cobalt Pyrogallol Red (PGR) complex on a stationary mercury drop electrode, followed by cathodic stripping voltAMmetry measurement of the reduction current of the adsorbed complex at –1.17 V (vs. Ag/AgCl). The optimum conditions for the determination of cobalt include pH 11.0, 35 μM Pyrogallol Red, an accumulation potential of –0.9 V (vs. Ag/AgCl) and scan rate 80 mV s-1. The peak current is proportional to the concentration of cobalt over the concentration range 5.0 to 280 ng mL-1 with a detection limit of 1 ng mL-1 and an accumulation time of 140 s. The method was applied to the determination of cobalt in analytical grade NaCl and water sAMples.

Keywords: adsorptive cathodic stripping voltAMmetry, Pyrogallol Red, Co(II) determination.

Full Article - PDF 207 KB Available OnLine: 04. 07. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 725–739 (2013)

UDC 628.3+66.061+546.56:628.336+66.046.59; JSCS–4453; doi: 10.2298/JSC120716125I; Original scientific paper

A solidification/stabilization process for wastewater treatment sludge from a primary copper smelter

DRAGANA IVŠIĆ-BAJČETA, ŽELJKO KAMBEROVIĆ*, MARIJA KORAĆ and MILORAD GAVRILOVSKI

Innovation Center of the Faculty of Technology and Metallurgy in Belgrade, University of Belgrade, Karnegijeva 4, 11000 Belgrade, Serbia

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

(Received 16 July, revised 19 November 2012)

Wastewater treatment sludge from a primary copper smelter is characterized as hazardous waste that requires treatment prior to disposal due to its significant contents of heavy metals and arsenic. The aim of the presented study was to investigate the feasibility and the effectiveness of a solidification/stabilization process of the sludge using fly ash and lime as binders. The effectiveness of the process was evaluated by Unconfined Compressive Strength (UCS) testing, leaching tests (EN 12457-4 and Toxicity Characteristic Leaching Procedure (TCLP)) and Acid Neutralization Capacity (ANC) tests. All the sAMples reached the target UCS value of 0.35 MPa. The calcium to silicon concentration ratio (cCa/cSi), determined by X-ray fluorescence analysis, was identified as main factor governing strength development. Inductively coupled plasma-optical emission spectrometry analyses of solutions after leaching tests showed excellent stabilization of Cu, Ni, Pb and Zn (above 99 %) and arsenic (above 90 %) in sAMples with high Ca(OH)2 content. Results of the ANC test indicated that the buffering capacity of solidified material linearly depended on Ca concentration in FA and lime. SAMples with 20 % of binder having 50 % of FA and 50 % of lime met all the requirements for safe disposal.

Keywords: fly ash; lime; heavy metals; unconfined compressive strength; leaching tests.

Full Article - PDF 245 KB Available OnLine: 20. 11. 2012. Cited by

J. Serb. Chem. Soc. 78 (5) 741–758 (2013)

UDC 550.378+546.791–78+520.84:550.389(397); JSCS–4454; doi: 10.2298/JSC120919124K; Original scientific paper

Discovery of uranium mineralizations in the rhyolite–granite complex in the Jabal Eghei area of southern Libya

JOVAN KOVAČEVIĆ, MEHDI BASHIR TEREESH*, MIRJANA B. RADENKOVIĆ** and ŠĆEPAN S. MILJANIĆ***

Geological Institute of Serbia, P. O. Box 42, 11000 Belgrade, Serbia

*Tajoura Nuclear Research Centre. P. O. Box 30878, Tajoura, Libya

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

***University of Belgrade, Faculty of Physical Chemistry, P. O. Box 47, 11158 Belgrade 118, Serbia

(Received 19 September, revised 12 November 2012)

During an investigation of the Jabal Eghei area in southern Libya and the production of geological maps on a scale of 1:250 000 (Tibesti sector, sheet Wadi Eghei NF 34-1 and NF 34-2), regional prospecting for mineral raw materials was performed. A radiometric survey of the observed targets at the sites indicated two significant uranium mineralizations in rhyolites, and some smaller ones in granites that are in close contact with rhyolites. Rhyolites are located in the central part of the investigated region. They cut through granite rocks. The first mineralization is in the central part of the rhyolite region, which is mostly composed of silificated rhyolites. The second one was discovered near the granite–rhyolite contact zone, characterized by the presence of silicified breccia rocks. These findings were confirmed by laboratory measurements of more than seventy sAMples collected in the area, using high-resolution gAMma-ray spectrometry. The concentrations of uranium in these mineralizations were found to range from approx. 50 mg kg-1 to more than 600 mg kg-1. The latter value is about 240 times above the Earth’s average. Besides uranium, these measurements have also given concentrations of thorium and potassium. Additional geochemical analysis was performed on sAMples taken from locations where uranium anomalies were discovered using the ICP-MS technique, in which the concentrations of more than forty elements were determined. The uranium mineralizations are accompanied by increased contents of silver (up to 17 times), arsenic (up to 8 times), molybdenum (up to 50 times), mercury (up to 9 times), and lead (up to 14 times), with regards to the Clark values. These results warrant a continued investigation of this region because of potential interest in the discovery of nuclear mineral raw materials.

Keywords: terrestrial radioactivity; Jabal Eghei; gAMma-ray spectrometry; uranium; mineralization; geological map.

Full Article - PDF 538 KB Supplementary Material PDF 147 KB Available OnLine: 14. 11. 2012. Cited by

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