JSCS Vol 80, No 6

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J. Serb. Chem. Soc. 80 (6) 731–738 (2015)

UDC 547.836.3+547.412.11:544.433.21+547–304.2+547.752+547.567; JSCS–4752; doi: 10.2298/JSC141124021I; Original scientific paper

 

An investigation of nucleophilic substitution reactions of 2,3-dichloro-1,4-naphthoquinone with various nucleophilic reagents

CEMIL IBIS, AHMED HASSEN SHNTAIF, HAKAN BAHAR and SIBEL SAHINLER AYLA

Department of Chemistry, Faculty of Engineering, Istanbul University, 34320, Avcilar, Istanbul, Turkey

 

(Received 24 November 2014, revised 26 February, accepted 1 March 2015)

Novel N-, N,S- and N,O-substituted naphthoquinone compounds were prepared by the reactions of 2,3-dichloro-1,4-naphthoquinone (1) and the cor­responding nucleophiles in the presence of chloroform and triethylamine or an ethanolic solution of Na2CO3. The structures of the novel naphthoquinone compounds were characterized by microanalysis, FT-IR, 1H-NMR, 13C-NMR, MS and cyclic voltammetry.

 

Keywords: 1,4-naphthoquinone; thioethers; amine; indolylquinones.

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J. Serb. Chem. Soc. 80 (6) 739–747 (2015)

UDC 547.821–116+547.828–116+542.913+547.587.51:615.28–188; JSCS–4753; doi: 10.2298/JSC140804004L; Original scientific paper

 

Synthesis of modified pyridine and bipyridine substituted coumarins as potent antimicrobial agents

HEMALI B. LAD, RAKESH R. GIRI, YOGITA L. CHOVATIYA and DINKAR I. BRAHMBHATT

Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar 388120, Gujarat, India

 

(Received 4 August 2014, revised 8 January, accepted 11 January 2015)

In the search for new antimicrobial agents, a series of new modified pyridine and bipyridine substituted coumarins 5ay was designed and syn­thesized by adopting a molecular hybridization strategy. All the synthesized compounds were evaluated for their in vitro antimicrobial activity using the broth dilution method against selected bacterial (Gram-positive and Gram-neg­ative) and fungal strains. Compounds 5a, 5f, 5g, 5n, 5r, 5t, 5w, 5x and 5y demonstrated promising antibacterial activity, while the other derivatives showed comparable activity to those of the standard drugs used as references.

 

Keywords: coumarins; bipyridines; Krohnke reaction; antimicrobial activity; broth dilution method.

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J. Serb. Chem. Soc. 80 (6) 749–754 (2015)

UDC 547.657:576.314:541.132.3; JSCS–4754; doi: 10.2298/JSC141201012P; Short communication

 

SHORT COMMUNICATION

The influence of naphthenic acids and their fractions on cell membrane permeability

KSENIJA PAVLOVIĆ, LJUBICA GRBOVIĆ, BOJANA VASILJEVIĆ, ANDREA ŽUPUNSKI*, MARINA PUTNIK-DELIĆ*, IVANA MAKSIMOVIĆ* and SLAVKO KEVREŠAN*

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, Serbia

*Faculty of Agriculture, University of Novi Sad, Trg Dositeja Obradovića 8, Serbia

 

(Received 1 December 2014, revised 29 January, accepted 3 February 2015)

The influence of naphthenic acids (NAs) mixture and their narrow fractions (called NA pH 4, pH 8 and pH 10) on the permeability of beetroot cell membrane was examined. The results showed that the effect depends on the treatment duration, concentration and the structures of the NAs. Longer treatment of plant cell membranes with sodium naphthenate (Na-naph) resulted in an increase in the membrane permeability (e.g., a 4-hour treatment with Na-naph (c = 100 μmol L-1) increased the membrane permeability by about 3 times, while prolongation of treatment to 24 h resulted in an 18-fold increase in the effect). NAs in the concentration range from 0.1 to 10 µmol L-1 did not change membrane permeability, while the membrane permeability increased linearly with increasing concentration from 10–100 μmol L-1. The fraction pH 8, where bi- and tricyclic carboxylic acids are the most abundant, expressed the strongest effect. These structures were predominant in the total NAs mixture as well. This could explain the similar, but slightly weaker effect of the mixture, compared to the effect of the NAs present in fraction pH 8. The effect of NAs on beetroot cell membrane was between the effects of the tested anionic (SDS and LS) and non-ionic surfactants (Triton X-100).

 

Keywords: naphthenic acids (NAs); naphthenic acid fractions; physiological activity; cell membranes permeability.

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J. Serb. Chem. Soc. 80 (6) 755–766 (2015)

UDC 547.1’13+546.814+547.78+547.367:615.281/.282–188; JSCS–4755; doi: 10.2298/JSC140711010P; Original scientific paper

 

Synthesis and spectroscopic characterization of mononuclear/binuclear organotin(IV) complexes with 1H-1,2,4-triazole-3-thiol: Comparative studies of their antibacterial/antifungal potencies

BUSHRA PARVEEN, IFTIKHAR HUSSAIN BUKHARI, SAIRA SHAHZADI*, SAQIB ALI*, SHABBIR HUSSAIN, KULSOOM GHULAM ALI and MUHAMMAD SHAHID**

Department of Chemistry, GC University, Faisalabad, Pakistan

*Department of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan

**Department of Chemistry and Biochemistry, University of Agriculture, Faisalabad-38000, Pakistan

 

(Received 11 July 2014, revised 30 January, accepted 21 February 2015)

A series of di- and tri-organotin(IV) complexes of the general for­mula, R2(Cl)SnL (1: R = Me; 2: R = Bu) and R3SnL (3: R = Bu; 4: R = Ph) were synthesized by refluxing equivalent molе ratios of organotin(IV) chlor­ides (R2SnCl2/R3SnCl) with 1H-1,2,4-triazole-3-thiol (LH) in dry methanol. The synthesized complexes (14) were further treated with CS2 and R2SnCl2/R3SnCl in 1:1:1 mole ratio to yield homobimetallic complexes of the types R2(Cl)SnLCS2Sn(Cl)R2 (5: R = Me; 6: R = Bu) and R3SnLCS2SnR3 (7: R = Bu; 8: R = Ph). The ligand and the complexes were characterized by ele­mental microanalysis (CHNS), FT-IR and multinuclear NMR (1H- and 13C-), and elec­tron ionization mass spectrometry. The IR data demonstrated that the dithio­carbamate donor site of the ligand acts in a bidentate manner and that the geometry around Sn(IV) is trigonal bipyramidal in the solid state. The 1H- and 13C-NMR data supported the tetrahedral geometry with thiol donor sites of the ligand while tetra- and penta-coordinated environments around dithiocarboxy­late bound tin(IV) in the solution state. Mass spectrometric data supported well the structures of the synthesized complexes. The homobimetallic derivatives were found more active than the mononuclear organotin(IV) compounds and free ligand against various strains of bacteria and fungi.

 

Keywords: homobimetallic complex; organotin chloride; NMR; IR; mass spec­tra; antimicrobial study; 1H-1,2,4-triazole-3-thiol; dithiocarboxylate.

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J. Serb. Chem. Soc. 80 (6) 767–777 (2015)

UDC 519.677+543.637:546.32+547.416+547.233’821:632.954; JSCS–4756; doi: 10.2298/JSC141224008M; Original scientific paper

 

Analysis of the chemical reactivity of aminocyclopyrachlor herbicide through the Fukui function

LUIS HUMBERTO MENDOZA-HUIZAR

Universidad Autónoma del Estado de Hidalgo, Área Académica de Química Químicas, Mineral de la Reforma, Hidalgo, C.P. 42186, México

 

(Received 25 December 2014, Accepted 25 January 2015)

The global and local DFT reactivity descriptors were calculated at the MP2/6-311++G (2d,2p) level of theory for aminocyclopyrachlor herbicide in the aqueous phase. Global reactivity descriptors, such as ionization energy, molecular hardness, electrophilicity and total energies, were calculated to evaluate the reactivity of aminocyclopyrachlor. The local reactivity was eval­uated through the Fukui function. The obtained results suggest that the cationic and dipolar forms of aminocyclopyrachlor exhibit similar global reactivity and are susceptible to de-amination and decarboxylation. In addition, opening of the ring might become feasible through free radical attacks on the neutral form, while a similar process is caused by nucleophilic attacks on the anionic form.

 

Keywords: aminocyclopyrachlor; reactivity; Fukui; MP2; PCM.

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J. Serb. Chem. Soc. 80 (6) 779–787 (2015)

UDC 546.57+539.12+549.67:544.726+66.094.2:546.49–71; JSCS–4757, doi: 10.2298/JSC140729020K; Original scientific paper

 

Anisotropic silver nanoparticles deposited on zeolite A for selective Hg2+ colorimetric sensing and antibacterial studies

ALIREZA KHORSHIDI, BEHROOZ HEIDARI and HAMIDREZA INANLU

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

 

(Received 29 July 2014, revised 24 February, accepted 26 February 2015)

Silver nanoparticles deposited on the surface of zeolite A were pre­pared via the post ion-exchange reduction and reduction–deposition methods. The formation of silver nanoparticles on the surface of zeolite A was verified by surface plasmon spectra using diffuse reflectance spectroscopy and ultra­violet–visible spectroscopy. The morphology of the prepared samples was characterized by X-ray diffraction and scanning electron microscopy. Further­more, silver nanoparticles deposited on the zeolite A after fixation of rhoda­mine B dye molecules on them were successful in the selective detection of Hg2+. After treatment with the so-obtained sensor, a colour change from col­ourless to pink was visible to the naked eye for concentrations of the Hg2+ solution down to 1.0×10-8 mol L-1. Antibacterial tests demonstrated the multi­functional application of the silver nanoparticles deposited on zeolite A.

 

Keywords: sensor; zeolite A; silver; nanoparticle; rhodamine B; mercury.

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J. Serb. Chem. Soc. 80 (6) 789–799 (2015)

UDC 577.164.1+544.6.076.32–039.26:543.552; JSCS–4758 doi:10.2298/JSC131216046K; Original scientific paper

 

Voltammetric determination of carbidopa and folic acid using a modified carbon nanotubes paste electrode

NASRIN KESHTKAR*,**, MOHAMMAD ALI TAHER* and HADI BEITOLLAHI***

*Department of Chemistry, Shahid Bahonar University of Kerman, P. O. Box 76175-133, Kerman, Iran

**Young Researchers Society, Shahid Bahonar University of Kerman, P. O. Box 76175-133, Kerman, Iran

***Environment Department, Institute of Science and High Technology and Environmental Sciences, Graduate University of Advanced Technology, Kerman, Iran

 

(Received 26 December 2013, revised 11 April, accepted 17 April 2014)

A novel electrochemical sensor for the selective and sensitive detect­ion of carbidopa in the presence of a large excess of folic acid at physiological pH was developed by the bulk modification of a carbon paste electrode (CPE) with carbon nanotubes (CNTs) and vinylferrocene. Large peak separation, good sensitivity and stability allow this modified electrode to be used for the analysis of carbidopa individually and simultaneously along with folic acid. Applying square wave voltammetry (SWV), a linear dynamic range of 1.0×10-67.0×10-4 M with a detection limit of 2.0×10-7 M was obtained for carbidopa. Finally, the proposed method was applied to the determination of carbidopa and folic acid in a urine sample.

 

Keywords: carbidopa; folic acid; carbon nanotubes; modified electrodes.

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J. Serb. Chem. Soc. 80 (6) 801–804 (2015)

UDC 546.34+546.33+546.3–71+544.6.076.2–145.2; JSCS–4759; doi: 10.2298/JSC141119127V; Extended abstract

 

EXTENDED ABSTRACT

Comparison of lithium and sodium intercalation materials·

MILICA VUJKOVIĆ

Faculty of Physical Chemistry, University in Belgrade, Studentski trg 12, 11000 Belgrade, Serbia

 

(Received 19 November, revised 14 December, accepted 25 December 2014)

The low abundance of lithium in the Earth’s crust and its high participation in overall cost of lithium-ion batteries incited intensive inves­tigation of sodium-ion batteries, in the hope that they may become similar in their basic characteristics: specific energy and specific power. Furthermore, over the last years, research has been focused on the replacement of the organic electrolytes of Li- and Na-ion batteries by aqueous electrolytes, in order to simplify the production and improve safety of use. In this lecture, some recent results on selected intercalation materials are presented: layered structure vanadium oxides, olivine and nasicon phosphates, potentially usable in both Li and Na aqueous rechargeable batteries. After their characterization by X-ray diffraction and electron microscopy, the electrochemical behavior was studied by both cyclic voltammetry and chronopotentiometry. By comparing the inter­calation kinetics and coulombic capacity of these materials in LiNO3 and NaNO3 solutions, it was shown that the following ones: Na1.2V3O8, Na2V6O16/C, NaFePO4/C and NaTi2(PO4)3/C may be used as electrode mater­ials in aqueous alkali-ion batteries.

 

Keywords: sodium and lithium storage capacity; metal-ion aqueous batteries.

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J. Serb. Chem. Soc. 80 (6) 805–817 (2015)

UDC 27–526.62:7.023.1–037.1+547.97–035.67:543.4+543.424.2; JSCS–4760; doi: 10.2298/JSC140722099D; Original scientific paper

 

Spectroscopic investigation of two Serbian icons painted on canvas

LJILJANA DAMJANOVIĆ, OLGICA MARJANOVIĆ, MILICA MARIĆ STOJANOVIĆ*, VELIBOR ANDRIĆ** and UBAVKA B. MIOČ

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

*National Museum Belgrade, Trg Republike 1a, 11000 Belgrade, Serbia

**University of Belgrade-Vinča Institute of Nuclear Sciences, P. O. Box 522, 11000 Belgrade, Serbia

 

(Received 22 July, revised 6 October, accepted 8 October 2014)

A multianalytical study of two Serbian icons, “The Virgin and Child” and “St. Petka”, painted on canvas by unknown authors was performed in order to identify the materials used as pigments, binders and the ground layer. The investigated icons belong to the Museum of the Serbian Orthodox Church in Belgrade. Samples, collected from different parts of the icons, were analysed by: optical microscopy (OM), energy dispersive X-Ray fluorescence (EDXRF), Fourier transform infrared (FTIR) and micro-Raman spectroscopy. The obtained results revealed the presence of the following pigments: Prussian Blue, ultramarine, Green Earth, iron oxides, Lead White and Zinc White. Lin­seed oil was used as the binder. The materials used for the ground layers were gypsum, calcite, baryte and Lead White. The gilded surface of the icon “The Virgin and Child” was made of gold. The gilded surface on the frame of this icon was made of imitation of gold, i.e., Schlagmetal, since EDXRF spectro­scopy showed the presence of copper and zinc, while gold was not detected. Based on the style and the consideration of an art historian, as well as on the obtained results for the corresponding pigments and binder, both icons were most probably made at the end of 19th or the beginning of the 20th century.

 

Keywords: pigments; EDXRF; FTIR spectroscopy; micro-Raman spectroscopy.

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J. Serb. Chem. Soc. 80 (6) 819–826 (2015)

UDC 549.67+547.466+678.743:615.281–188; JSCS–4761; doi: 10.2298/JSC141225017M; Original scientific paper

 

Antibacterial activity of copper-containing clinoptilolite/PVC composites toward clinical isolate of Acinetobacter baumannii

JELENA K. MILENKOVIĆ, JASNA J. HRENOVIĆ*, IVANA S. GOIĆ-BARIŠIĆ**, MILOŠ D. TOMIĆ AND NEVENKA Z. RAJIĆ***1Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade, 11000 Belgrade, Serbia

*Faculty of Science, Division of Biology, University of Zagreb, 10000 Zagreb, Croatia

**Split University Hospital and School of Medicine, Department of Clinical Microbiology, University of Split, 21000 Split, Croatia

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

 

(Received 25 December 2014, revised 13 February, accepted 18 February 2015)

The multidrug-resistant bacteria Acinetobacter baumannii cause serious hospital infections. Commercial poly(vinyl chloride) (PVC) used for endotracheal tubes was modified in order to obtain a composite with an anti­bacterial effect towards a clinical isolate of A. baumannii ST145. The com­posites were prepared by addition of different amounts of copper-containing zeolite tuff (CuZ) and by successive impregnation with D-tyrosine (D-Tyr) solution. The composites that were obtained by addition of CuZ (CuZ–PVC) only did not exhibit an antibacterial effect. The impregnation of the CuZ–PVC by D-Tyr resulted in an antibacterial effect which was explained by a syner­gistic effect of CuZ and D-Tyr. Rheological tests confirmed that the modi­fication of PVC by CuZ does not affect its processability and reformability.

 

Keywords: natural zeolite; multidrug resistance; polymers; poly(vinyl chlo­ride); amino acids.

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J. Serb. Chem. Soc. 80 (6) 827–838 (2015)

UDC 628.336+546.47/.49’56’815:504.054:628.515/.516; JSCS–4762; doi: 10.2298/JSC140317047G; Original scientific paper

 

Heavy metals in Neogene sedimentary rocks as a potential geogenic hazard for sediment, soil, and surface and groundwater contamination (eastern Posavina and the Lopare Basin, Bosnia and Herzegovina)

NENAD GRBA*,**, FRANZ NEUBAUER**, ALEKSANDRA ŠAJNOVIĆ***, KSENIJA STOJANOVIĆ* and BRANIMIR JOVANČIĆEVIĆ*

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

**Paris Lodron University of Salzburg, Department of Geography and Geology, Hellbrunnerstrasse 34,5020 Salzburg, Austria

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

 

(Received 17 March, revised 28 April, accepted 29 April 2014)

The influence of geochemical processes (weathering, erosion and dilution) of the Internal Dinarides to the Posavina Neogene Basin and their implication to the pollution of the Sava River sediments at four sampling sites in the Eastern Posavina (Županja, Brčko, Bosanska Rača and Sremska Mitro­vica) was studied. For this purpose, comparison of contents of heavy metals (Pb, Zn, Cu, Ni, Cr, Cd, As and Hg) of the Eastern Posavina sediments with local background values was performed. Sediments from two boreholes of the Lopare Basin considered as non-polluted and representative for specific geo­logic and hydrogeologic system were used for the calculation of local back­ground values. The aim was to assess whether the observed heavy metals concentrations at four sampling sites along the Sava River represent back­ground/natural or anthropogenic contamination. This task was performed using the geo-accumulation index and total enrichment factor. According to values of the total enrichment factor (0.25–0.71), the anthropogenic impact on the investigated area was quite low. The heavy metals contents in river sediments, soil and groundwater were mainly controlled by geochemical processes, parti­cularly weathering (chemical proxy of alteration value ≈ 60). The results also offer novel insights into the elevated geogenic levels of Cr and Ni in the East­ern Posavina region.

 

Keywords: pollution; river sediments; geo-accumulation index; total enrich­ment factor; weathering.

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June 28. 2015.

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