JSCS Vol 74, No. 2

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J. Serb. Chem. Soc. 74 (2) 103–115 (2009)
UDC 547.71+547.74+542.913:615.281–188; JSCS–3813; doi: 10.2298/JSC0902103H; Original scientific paper

Synthesis, reactions and biological activity of 3-arylidene-5-(4-methylphenyl)-2(3H)-furanones
ASIF HUSAIN, M. MUMTAZ ALAM and NADEEM SIDDIQUI
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, JAMia HAMdard (HAMdard University), New Delhi - 110 062, India

(Received 10 March, revised 20 September 2008)

3-Arylidene-5-(4-methylphenyl)-2(3H)-furanones 2a–m were prepared from 3-(4-methyl-benzoyl)propanoic acid 1 and several aromatic aldehydes. Some of the selected furanones were reacted with AMmonia gas and benzylAMine to give corresponding 3-arylidene-1,3-dihydro-5-(4-methylphenyl)-2H-pyrrol-2-ones 3a–h and 3-arylidene-1-benzyl-1,3-dihydro-5-(4-methylphenyl)-2H-pyrrol-2-ones 4a–f, respectively, which were characterized on the basis of IR, 1H-NMR, mass spectral data and elemental analysis results. These compounds were tested for their anti-inflAMmatory and antibacterial activities. The compounds, which showed significant anti-inflAMmatory activity, were further screened for their analgesic and ulcerogenic activities. Three new compounds (2e, 2h and 4d), out of twenty-seven showed very good anti-inflAMmatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. The antibacterial activity is expressed as the corresponding MIC values.

 

Keywords: furanone; pyrrolone; anti-inflAMmatory; analgesic; antibacterial activity.

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J. Serb. Chem. Soc. 74 (2) 117–128 (2009)
UDC 634.22/.23:663.5:541.4+541.18.045; JSCS–3814; doi: 10.2298/JSC0902117T; Original scientific paper

Characterization of volatile compounds of “Drenja”, an alcoholic beverage obtained from the fruits of cornelian cherry
VELE TEŠEVIĆ, NINOSLAV NIKIĆEVIĆ*, SLOBODAN MILOSAVLJEVIĆ, DANICA BAJIĆ**, VLATKA VAJS**, IVAN VUČKOVIĆ**, LJUBODRAG VUJISIĆ**, IRIS ĐORĐEVIĆ***, MIROSLAVA STANKOVIĆ**** and MILOVAN VELIČKOVIĆ*
Faculty of Chemistry, University of Belgrade, Studentski trg 16, 11000 Belgrade, Serbia
*Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11080 Zemun, Serbia

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

***Faculty for Veterinary Medicine, University of Belgrade, Bulevar oslobođenja 18, 11000 Belgrade, Serbia
****Physical Chemistry Laboratory, Institute of Nuclear Science Vinča, 11001 Belgrade, Serbia


(Received 17 June, revised 8 September 2008)

In this study, volatile compounds were analyzed in five sAMples of home-made spirit beverage made by the distillation of fermented fruits of cornelian cherry (Cornus mas L.). The major volatile compounds, besides ethanol, identified and quantified were: methanol, acetaldehyde, 1-propanol, ethyl acetate, 2-methyl-1-propanol, 1-butanol, AMyl alcohols, 1-hexanol and 2-phenylethanol. The minor volatiles were submitted to liquid–liquid extraction with dichloromethane and analyzed by gas chromatography and gas chromatography/ /mass spectrometry (GC/MS). A total of 84 compounds were identified. The most abundant compounds were straight-chain free fatty acids, ethyl esters of C6–C18 acids, limonene, 2-phenylethanol and 4-ethylphenol. Most of the compounds found in the “Drenja” spirits investigated in this study are similar to those present in other alcoholic beverages.

 

Keywords: Cornus mas; alcoholic beverage; fruit spirits; Cornelian cherry spirit; volatiles; GC/MS.

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J. Serb. Chem. Soc. 74 (2) 129–132 (2009)
UDC 582.684.1:577.121:547.583.1(549.1); JSCS–3815; doi: 10.2298/JSC0902129A;  Short communication

SHORT COMMUNICATION

Secondary metabolites of Hypericum monogynum from Pakistan
MOHAMMAD ARFAN, NAILA RAZIQ, IVANA ALJANČIĆ* and SLOBODAN MILOSAVLJEVIĆ**

Institute of Chemical Science, Peshawar University, 25000 Peshawar, Pakistan

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

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

(Received 26 May, revised 15 October 2008)

4-Chlorobenzoic acid (1), quercitrin (2), astilbin (3), along with β-sitosterol, γ-sitosterol, friedelin and β-AMyrin were isolated from the aerial parts of Hypericum monogynum. Whereas compound 1 was isolated for the first time from natural sources, flavanonol 3 was not found before in these species.

 

Keywords: Hypericum monogynum; Clusiaceae; 4-chlorobenzoic acid; quercitrin; astilbin.

Full Article - PDF 157 KB

J. Serb. Chem. Soc. 74 (2) 133–139 (2009)
UDC 639.61+665.12+577.115:615.281–188; JSCS–3816; doi: 10.2298/JSC0902133M; Original scientific paper

Comparison of the antibacterial activity, volatiles and fatty acid composition of lipids of Phycopsis species collected at different locations from the Bay of Bengal (Orissa coast)
PRAVAT MANJARI MISHRA and AYINAMPUDI SREE
Natural Product Department, Institute of Minerals &AMp; Materials Technology (Formerly RRL), Bhubaneswar - 751013, Orissa, India


(Received 30 May, revised 7 August 2008)

The fatty acid composition as well as the volatiles and an antibacterial screening of the total lipids isolated from marine sponge Phycopsis sp. collected at two different locations from the Bay of Bengal of the Orissa coast having different morphological features were studied. The content of linear saturated acids was 30.25 % in Phycopsis sp. 1, while their content reached 50.33 % in Phycopsis sp. 2. The AMount of monobranched, saturated acids was 44.87 % in Phycopsis sp.1 and 38.83 % in Phycopsis sp. 2. There was more phytanic acid (7.92 %) in Phycopsis sp. 2 than in Phycopsis sp. 1 (4.06 %). The AMount of 5,9‑pentacosadienoic acid was found to be 5.54 % in Phycopsis sp. 1, while it was absent in Phycopsis sp. 2. Both species showed differences in their fatty acid composition and volatiles as well as in the antibacterial screening of their lipid extracts.

 

Keywords: sponges; Phycopsis sp.; fatty acids; volatiles; antibacterial.

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J. Serb. Chem. Soc. 74 (2) 141–154 (2009)

UDC 547.551+542.913:577:547.213–32:547.581.2; JSCS–3817; doi: 10.2298/JSC0902141S; Original scientific paper

 

Synthesis, coordination and biological aspects of organotin(IV) derivatives of 4-[(2,4-dinitrophenyl)AMino)]-4-oxo-2-butenoic acid and 2-{[(2,4-dinitrophenyl)AMino]carbonyl}benzoic acid

KHADIJA SHAHID, SAIRA SHAHZADI* and SAQIB ALI

Department of Chemistry, Quaid-i-AzAM University, IslAMabad – 45320, Pakistan

*Department of Chemistry, GC University, Faisalabad, Pakistan

 

(Received 29 February, revised 13 June 2008)

New series of organotin(IV) complexes of aniline derivatives, R2SnL2 and R3SnL [where R = Me, n-Bu, Ph, n-Oct] have been synthesized by the reaction of HL1 and HL2 with respective organotin halides or oxides. Experimental details for the preparation and characterization (including elemental analysis, IR and multinuclear NMR (1H-, 13C- and 119Sn-) spectra in CDCl3 and EI mass spectra of both series are provided. The binding sites of the ligands were identified by means of FTIR spectroscopic measurements. It was found that in all cases the organotin(IV) moiety reacts with the oxygen of COO group to form new complexes. In the diorganotin complexes, the COO group is coordinated to the organotin(IV) centres in a bidentate manner in the solid state. The 119Sn NMR data and the nJ(13C‑119/117Sn) coupling constant support the tetrahedral coordination geometry of the organotin complexes in non-coordinating solvents. Biological activities (antibacterial, antifungal, cytotoxicity, antileishmanial and insecticidal) of these compounds are also reported.

 

Keywords: organotin(IV) carboxylates; IR; multinuclear NMR (1H, 13C and 119Sn); mass spectrometry; biological activity.

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J. Serb. Chem. Soc. 74 (2) 155–158 (2009)

UDC 537.872+539.124:541.5; JSCS–3818; doi: 10.2298/JSC0902155R; Short communication

 

SHORT COMMUNICATION

Stability order of isomeric benzenoid hydrocarbons and Kekulé structure count

SLAVKO RADENKOVIĆ and IVAN GUTMAN

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

 

(Received 10 September 2008)

The commonly accepted opinion that the thermodynAMic stability of isomeric benzenoid hydrocarbons (assessed by their total π-electron energy and various resonance energies) increases with increasing number of Kekulé structures is shown to be violated in numerous cases. The smallest exAMples of such anomalous behavior are two hexacyclic pericondensed benzenoids of formula C24H14 and several pairs of heptacyclic catacondensed benzenoids of formula C30H18.

 

Keywords: total π-electron energy; Kekulé structures; benzenoid hydrocarbons.

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J. Serb. Chem. Soc. 74 (2) 159–169 (2009)

UDC 547.653+543.4/.5:544.351–145.82:544.362:546.212; JSCS–3819; doi: 10.2298/JSC0902159M; Original scientific paper

 

Spectrophotometric determination of the acidity constants of calcon in water and mixed water–organic solvents

MOHAMMAD MAZLOUM-ARDAKANI, SHAHRAM LOTFI*, JAHANBAKHSH GHASEMI**, ALAHDAD SHABABI* and MOHAMMAD NOROOZI***

Department of Chemistry, Faculty of Science, Yazd University, Yazd, Iran

*Department of Chemistry, PayAMe Noor University, GilaneGharb Unit, Gilane Gharb, Iran

**Department of Chemistry, Faculty of Science, Razi University, Kermanshah, Iran
***Research Institute of Petroleum Industry, Kermanshah Research Center of Oil and Engineering, Kermanshah, Iran

 

(Received 27 November, revised 19 July 2008)

The acid–base properties of calcon (1-(2-hydroxy-1-naphthylazo)-2-naphthol-4-sulfonic acid) in water and mixed water–organic solvents at 25 °C at an ionic strength of 0.10 M are studied by a multiwavelength spectrophotometric method. The organic solvents used were the AMphiprotic (methanol), dipolar aprotic (dimethylsulfoxide), and low basic aprotic (acetonitrile). To evaluate the pH absorbance data, a resolution method based on the combination of soft- and hard-modeling was applied. The acidity constants of all related equilibria were estimated using the whole spectral fitting of the collected data to an established factor analysis model. The data analysis progrAM Datan was applied for determination of the acidity constants. The corresponding pKa values were determined in water and mixed water–organic solvents. Linear relationship between the acidity constants and the mole fraction of the different sol-vents in the mixtures exist. The effect of solvent properties on acid–base behavior is discussed.

 

Keywords: calcon; Datan; spectrophotometry; organic solvents; acidity constants.

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J. Serb. Chem. Soc. 74 (2) 171–182 (2009)

UDC 547.451:547.831:531.3+541.124:547.461.2+54–145.2; JSCS–3820; doi: 10.2298/JSC0902171R; Original scientific paper

 

Kinetics and mechanism of the oxidation of some substituted aldonitrones by quinolinium chlorochromate in aqueous DMF medium in the absence and presence of oxalic acid

GOVINDASAMY RAJARAJAN, NATESAN JAYACHANDRAMANI*, SUBRAMANIAN MANIVARMAN, JAYARAMAN JAYABHARATHI and VENUGOPAL THANIKACHALAM

Department of Chemistry, AnnAMalai University, AnnAMalainagar - 608 002, TAMil Nadu, India

*Department of Chemistry, Pachaiyappa’s College, Chennai - 600 030, India

 

(Received 31 December 2007, revised 16 May 2008)

The kinetics of the oxidation of aldonitrones (nitrone) by quinolinium chlorochromate (QCC) was determined in 50 % DMF–water in the absence and presence of oxalic acid in order to study the effect of oxalic acid. It was considered worthwhile to investigate whether it undergoes co-oxidation or just functions as a catalyst in the reaction. The reaction was followed iodometrically. Under the employed experimental conditions, the reaction is first order each with respect to concentration of nitrone, QCC, and oxalic acid and fractional order with respect to H+ concentration. There was no discernible effect with increasing in ionic strength but the rate of oxidation decreased with decreasing dielectric constant of the medium. Addition of MnSO4 had a significant and acrylonitrile no effect on the reaction rate. A mechanism involving protonated nitrone and QCC as the reactive oxidant is proposed. The activation parAMeters were calculated and are presented.

 

Keywords: aldonitrones; quinolinium chlorochromate; isokinetic plot; entropy; enthalpy; free energy; oxalic acid.

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J. Serb. Chem. Soc. 74 (2) 183–196 (2009)        

UDC 541.44–034+546.33’271–386:66.074.36; JSCS–3821, doi: 10.2298/JSC0902183B; Review paper

 

REVIEW PAPER

Hydrogen storage in complex metal hydrides

BORISLAV BOGDANOVIĆ, MICHAEL FELDERHOFF and GUIDO STREUKENS

Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470 Mülheim a. d. Ruhr, Germany

 

(Received 16 June, revised 10 October 2008)

Complex metal hydrides such as sodium aluminohydride (NaAlH4) and sodium borohydride (NaBH4) are solid-state hydrogen-storage materials with high hydrogen capacities. They can be used in combination with fuel cells as a hydrogen source thus enabling longer operation times compared with classical metal hydrides. The most important point for a wide application of these materials is the reversibility under moderate technical conditions. At present, only NaAlH4 has favourable thermodynAMic properties and can be employed as a thermally reversible means of hydrogen storage. By contrast, NaBH4 is a typical non- -reversible complex metal hydride; it reacts with water to produce hydrogen.

 

Keywords: complex hydrides; sodium alanate; sodium aluminohydride; sodium borohydride; hydrogen storage.

Full Article - PDF 255 KB

J. Serb. Chem. Soc. 74 (2) 197–202 (2009)

UDC 621.377.6+778.38:620.193.4:66–952:519.687; JSCS–3822; doi: 10.2298/JSC0902197J; Short communication

 

SHORT COMMUNICATION

Mapping the concentration changes during the dynAMic processes of crevice corrosion by digital

holographic reconstruction

HENGLEI JIA*, SHENHAO CHEN*,****, BOYU YUAN**, CHAO WANG***,**** and LIANG LI***

*Department of Chemistry, Shandong University, Jinan 250100, P. R. China

**Department of Physics, Xuzhou Normal University, Xuzhou 221116, P. R. China

***Department of Chemistry, Xuzhou Normal University, Xuzhou 221116, P. R. China

****State Key Laboratory for Corrosion and Protection, Shenyang 110016, P. R. China

 

(Received 7 July, revised 27 August 2008)

The dynAMic process of crevice corrosion during anodic dissolution of a crevice electrode in a 5.0 mmol dm-3 NaCl solution has been studied by digital holographic reconstruction. Digital holographic reconstruction has been proved to be an effective and in situ technique to detect the changes in the solution concentration because useful and direct information can be obtained from the three-dimensional images. It provides a valuable method for a better understanding of the mechanism of crevice corrosion by studying the dynAMic processes of changes in the solution concentration at the interface of crevice corrosion.

 

Keywords: digital holography; crevice corrosion; numerical reconstruction; phase difference; concentration change.

Full Article - PDF 317 KB

J. Serb. Chem. Soc. 74 (2) 203–211 (2009)

UDC 669.112.227+669.295.86+544.032.4; JSCS–3823; doi: 10.2298/JSC0902203B; Original scientific paper

 

Titanium diffusion coatings on austenitic steel obtained by the pack cementation method

MIRELA BRITCHI, NICULAE ENE, MIRCEA OLTEANU and CONSTANTIN RADOVICI*

Romanian Academy, Institute of Physical Chemistry “Ilie Murgulescu”, Splaiul Independentei, 202, Bucharest, Romania

*ICECHIM, Splaiul Independentei, 202, Bucharest, Romania

 

(Received 21 March, revised 25 June 2008)

The surface of specimens made of 316L austenitic steel was modified by titanium diffusion. The diffusion coatings were obtained by packing in a powder mixture consisting of titanium powder, NH4Cl and Al2O3 powder. The procedure required high temperatures, over 900 °C, and long durations. Atomic titanium was formed in the muffle during the process. Titanium atoms from the metallic part surfaces diffuse towards the interior and a diffusion layer is formed as a function of the steel composition. Titanium diffusion into the surface of 316L austenitic steel determines the formation of a complex coating: a thin layer of TiN at the exterior and a layer consisting of compounds containing Ti, Ni and Fe in the interior of the coating. The obtained coatings were continuous, adherent and had a hardness higher than that of the substrate material. The diffusion coatings were investigated by optical and electron microscopy, X-ray diffraction and Vickers microhardness tests.

 

Keywords: titanium diffusion coatings on 316L austenitic steel; pack cementation method.

Full Article - PDF 1,370 KB

J. Serb. Chem. Soc. 74 (2) 213–221 (2009)

UDC 669.3+544–145.15+661.224+622.772:621.928.46; JSCS–3824; doi: 10.2298/JSC0902213C; Original scientific paper

 

Mesophilic leaching of copper sulphide sludge

VLADIMIR B. CVETKOVSKI, VESNA T. CONIĆ, MILOVAN VUKOVIĆ* and MILENA V.CVETKOVSKA**

Mining and Metallurgy Institute, Bor, Serbia

*Technical Faculty, University of Belgrade, Bor, Serbia

**Faculty of Chemistry, University of Belgrade, Belgrade, Serbia

 

(Received 16 May, revised 24 June 2008)

Copper was precipitated using a sodium sulphide solution as the precipitation agent from an acid solution containing 17 g/l copper and 350 g/l sulphuric acid. The particle size of nearly 1 µm in the sulphide sludge sAMple was detected by optical microscopy. Based on chemical and X-ray diffraction analyses, covellite was detected as the major sulphide mineral. The batch bioleach AMenability test was performed at 32 °C on the Tk31 mine mesophilic mixed culture using a residence time of 28 days. The dissolution of copper sulphide by direct catalytic leaching of the sulphides with bacteria attached to the particles was found to be worthy, although a small quantity of ferrous ions had to be added to raise the activity of the bacteria and the redox potential of the culture medium. Throughout the 22-day period of the bioleach test, copper recovery based on residue analysis indicated a copper extraction of 95 %, with copper concentration in the bioleach solution of 15 g/l. The slope of the straight line tangential to the exponential part of the extraction curve gave a copper solubilisation rate of 1.1 g/l per day. This suggests that a copper extraction of 95 % for the period of bioleach test of 13.6 days may be attained in a three-stage bioreactor system.

 

Keywords: copper; acid solutions; hydrogen sulphide; sulphide sludge; bio-leaching.

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Copyright &AMp; copy; SHD 2009.
February 12, 2009.
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