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.
Full
Article - PDF 212 KB
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.
Full Article - PDF 244 KB
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.
Full Article - PDF 202 KB
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.
Full Article - PDF 229 KB
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.
Full Article - PDF 214 KB
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.
Full Article - PDF 1,517 KB
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
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.
Full Article - PDF 202 KB
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.
Full Article - PDF 234 KB
Copyright
&AMp; copy; SHD 2009.
February 12, 2009.
For more information contact: JSCS@tmf.bg.ac.rs