J. Serb. Chem. Soc. 74 (8–9) 847–855 (2009)
UDC 547.272’11+547.564.7:542.913:547–304.6; JSCS–3881; doi: 10.2298/JSC0909847I; Original scientific paper

The synthesis and characterization of some novel 5-chloro-2-(substituted alkoxy)-N-phenylbenzAMide derivatives
IOANA M. C. IENAŞCU*^,***, ALFA X. LUPEA*, IULIANA M. POPESCU**, MIRABELA A. PĂDURE* and ALINA D. ZAMFIR***^,****

*Politechnica University, Faculty of Industrial Chemistry and Environment Engineering, Department of Organic Chemistry, 2 P-ţa Victoriei, 300006 Timisoara, Romania

**Banat’s Agricultural Science University, Faculty of Agriculture, Department of Chemistry and Biochemistry, 119 Calea Aradului, 300645 Timisoara, Romania

***Mass Spectrometry Laboratory, National Institute for Research and Development in Electrochemistry and Condensed Matter, 1 Plautius Andronescu, 300224 Timisoara, Romania

****Aurel Vlaicu University of Arad, 77 Revoluţiei Blvd., 310130 Arad, Romania

(Received 26 November 2007, revised 27 April 2009)

To obtain biologically active compounds, the synthesis of some new derivatives with an o-hydroxybenzAMide structure was performed. The ethyl esters 4–6 were obtained by the reaction of 5-chloro-2-hydroxy-N-phenylbenzAMide and chloro-substituted acid ethyl esters 1–3 in ethyl methyl ketone. The obtained ethyl esters were condensed with hydrazine yielding the hydrazides 7–8. The hydrazones 11–14 were obtained by the reaction of the hydrazides and the chloro-substituted benzaldehydes 9–10. All the newly synthesized compounds were characterized by FTIR, ¹H-NMR, ¹³C-NMR, MS and elemental analyses.

Keywords: 5-chloro-2-(substituted alkoxy)-N-phenylbenzAMide derivatives; ethyl esters; hydrazides; hydrazones; O-substituted salicylanilides.

J. Serb. Chem. Soc. 74 (8–9) 857–865 (2009)
UDC 547.933+66.094.3:633.34; JSCS–3882; doi: 10.2298/JSC0909857K; Original scientific paper

The effect of cholic acid treatment on the oxidative status of soybean plants
SLAVKO E. KEVREŠAN, ĐORĐE R. MALENČIĆ, MILAN T. POPOVIĆ, KSENIJA N. KUHAJDA* and JULIJAN E. KANDRAČ
Faculty of Agriculture, University of Novi Sad, Trg Dositeja Obradovića 8, 21000 Novi Sad, Serbia

*Faculty of Science, Department of Chemistry, University of Novi Sad, Trg Dositeja Obradovića 3, 21000 Novi Sad, Serbia

(Received 18 February, revised 29 March 2009)

The objective of this work was to study the effect of treatment of young soybean plants with cholic acid of different concentrations on their oxidative status. Young soybean plants, grown hydroponically for two weeks, were treated by adding cholic acid to the nutrient solution at the concentrations 20, 40, 60 and 80 mg/L, the control being without cholic acid. After one week, several parAMeters of the oxidative status were determined in the leaves and roots of the plants: contents of superoxide (O^₂^-), hydroxyl radicals (^•OH) and glutathione (GSH), lipid peroxidation (LP), the superoxide dismutase (SOD) activity and the soluble protein accumulation, as well as the contents of chlorophylls and carotenoids. Treatments with cholic acid increased O^₂^-, LP, •OH and GSH in the leaves of the treated plants, while only the OH content in-creased in the roots at higher cholic acid concentrations. The obtained results support the idea that cholic acid, as an elicitor of defence responses in plants, might act through the generation of an oxidative burst.

Keywords: cholic acid; soybean; oxidative status.

J. Serb. Chem. Soc. 74 (8–9) 867–883 (2009)
UDC 547.367:547.96+66–96+547.444; JSCS–3883; doi: 10.2298/JSC0909867A;  Original scientific paper

The role of the thiol group in protein modification with methylglyoxal
JELENA M. AĆIMOVIĆ, BOJANA D. STANIMIROVIĆ and LJUBA M. MANDIĆ

Faculty of Chemistry, Department of Biochemistry, University of Belgrade, P.O. Box 51, 11158 Belgrade, Serbia

(Received 26 November 2008, revised 9 February 2009)

Methylglyoxal is a highly reactive α-oxoaldehyde with elevated production in hyperglycemia. It reacts with nucleophilic Lys and Arg side-chains and N-terminal AMino groups causing protein modification. In the present study, the importance of the reaction of the Cys thiol group with methylglyoxal in protein modification, the competitiveness of this reaction with those of AMino and guanidine groups, the time course of these reactions and their role and contribution to protein cross-linking were investigated. Human and bovine serum albumins were used as model systems. It was found that despite the very low levels of thiol groups on the surface of the exAMined protein molecules (approx. 80 times lower than those of AMino and guanidino groups), a very high percentage of it reacts (25–85 %). The AMount of reacted thiol groups and the rate of the reaction, the time for the reaction to reach equilibrium, the formation of a stable product and the contribution of thiol groups to protein cross-linking depend on the methylglyoxal concentration. The product formed in the reaction of thiol and an insufficient quantity of methylglyoxal (compared to the concentrations of the groups accessible for modification) participates to a significant extent (4 %) to protein cross-linking. Metformin applied in equimolar concentration with methylglyoxal prevents its reaction with AMino and guanidino groups but, however, not with thiol groups.

Keywords: methylglyoxal; protein thiol group reaction; protein modification and cross-linking; AGEs.

J. Serb. Chem. Soc. 74 (8–9) 885–892 (2009)
UDC 633.31:547.992+54–74:661.185.6–32; JSCS–3884; doi: 10.2298/JSC0909885M; Original scientific paper

Changes in the infrared attenuated total reflectance (ATR) spectra of lignins from alfalfa stem with growth and development
JORDAN P. MARKOVIĆ, JASMINA B. RADOVIĆ, RATIBOR T. ŠTRBANOVIĆ, DANICA S. BAJIĆ* and MIROSLAV M. VRVIĆ*^,**
Institute for Forage Crops, 37000 Kruševac, Trg Kosturnica 50, 37000, Serbia

*Department of Chemistry, Institute of Chemistry, Technology and Metallurgy,11001 Belgrade, Njegoševa 12, P.O. Box 473, Belgrade, Serbia

**Faculty of Chemistry, University of Belgrade, 11158 Belgrade, Studentski trg 16, P.O. Box 51, Belgrade, Serbia

(Received 24 February, revised 30 March 2009)

Lignin is a poorly characterized polymer and its exact properties vary depending on both the species of the plant and its location within the plant. Three classes of lignins taken from alfalfa stem were exAMined. The investigation was concentrated on the determination of chemical changes in the lignins during growth and development by the attenuated total reflectance (ATR) infrared (IR) spectrometric technique. The spectrum of permanganate lignin was comparable to that of acid detergent lignin. The main differences were in the different relative absorbance of the peaks. The predominant component of acid detergent lignin and permanganate lignin was guaiacyl-type lignin. The predominant component of Klason lignin was syringyl-type lignin. A comparison between the signals from lignin in different development stages revealed the appearance of new peaks, which are indications of new bonds and changes in the structure of the lignins.

Keywords: alfalfa; acid detergent; permanganate and Klason lignin; АТR infrared spectra.

J. Serb. Chem. Soc. 74 (8–9) 893–906 (2009)
UDC 577.15+582.734.3:633.71+635.074:57.016.4; JSCS–3885; doi: 10.2298/JSC0909893D; Original scientific paper

J. Serb. Chem. Soc. 74 (8–9) 907–915 (2009)

J. Serb. Chem. Soc. 74 (8–9) 917–926 (2009)

UDC 542.913:667.281+544.142.5:615.281–188; JSCS–3887; doi: 10.2298/JSC0909917K; Original scientific paper

J. Serb. Chem. Soc. 74 (8–9) 927–938 (2009)

546.732’562’742+547.77+547–304.6:615.281–188; JSCS–3888; doi: 10.2298/JSC0909927T; Original scientific paper

Synthesis, spectral studies and antibacterial activity of Cu(II), Co(II) and Ni(II) complexes of 1-(2-hydroxyphenyl)-3-phenyl-2-propen-1-one, N²-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]hydrazone

PAULMONY THARMARAJ, DEIVASIGAMANI KODIMUNTHIRI, CLARENCE D. SHEELA* and CHAPPANI S. SHANMUGA PRIYA

Department of Chemistry, Thiagarajar College, Madurai-625009, India

*Department of Chemistry, the American College, Madurai-625002, India

(Received 6 January, revised 16 April 2009)

A new series of Cu(II), Co(II) and Ni(II) complexes with the 1-(2-hydroxyphenyl)-3-phenyl-2-propen-1-one, N²-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]hydrazone ligand, C₂₁H₂₂N₄O (LH), were synthesized by the reaction of 1-(2-hydroxyphenyl)-3-phenyl-2-propen-1-one, hydrazone with (3,5-dimethyl-1H-pyrazol-1-yl)methanol and characterized. The nature of the bonding and geometry of the complexes were deduced from elemental analysis, IR, electronic and ¹H-NMR spectroscopy, and magnetic susceptibility and conductivity measurements. The studies indicated square-planar, tetrahedral and octahedral geometry for the copper(II), cobalt(II) and nickel(II) complexes, respectively. The ESR spectra of the copper(II) complex in acetonitrile at 300 and 77 K were recorded and their salient features are reported. The electrochemical behavior of the copper (II) complex was studied by cyclic voltAMmetry. The antimicrobial activity of the ligand and its metal complexes were studied against the following strains of microorganism: Staphylococcus aureus, Salmonella enterica typhi, Escherichia coli and Bacillus subtilis by the well diffusion method. Metal complexes showed enhanced antimicrobial activity compared with that of the free ligand.

Keywords: 3,5-dimethyl-1-(hydroxymethyl)pyrazole; 2’-hydroxychalcone; metal complexes; pyrazole; Cu(II), Co(II) and Ni(II) complexes; antimicrobial activity.

J. Serb. Chem. Soc. 74 (8–9) 939–951 (2009)     

UDC 546.732’742’562’472:547.217.2+547.556.3:541.123.2; JSCS–3889, doi: 10.2298/JSC0909939F; Original scientific paper

Metal ion controlled synthesis of 16- and 18-membered binuclear octaazAMacrocyclic complexes with Co(II), Ni(II), Cu(II) and Zn(II): a comparative spectroscopic approach to DNA binding to Cu(II) complexes

FARHA FIRDAUS, KANEEZ FATMA, ASAD U. KHAN* and MOHAMMAD SHAKIR

Division of Inorganic Chemistry, Department of Chemistry, Aligarh Muslim University, Aligarh-202002, India

*Interdisciplinary Biotechnology Unit, Aligarh Muslim University, Aligarh-202002, India

(Received 12 January, revised 7 May 2009)

A series of 16- and 18-membered binuclear octaazAMacrocyclic complexes, [M₂L₁(NO₃)₄] and [M₂L₂(NO₃)₄] (M = Co(II), Ni(II), Cu(II), Zn(II), L1 = 3,8,11,16-tetrAMethyl-1,2,4,7,9,10,12,15-octaaza-3,7,11,15-cyclohexadecatetraene and L₂ = 3,9,12,18-tetrAMethyl-1,2,4,8,10,11,13,17-octaaza-3,8,12,17-cyclooctadecatetraene) were synthesized by metal template condensation of N,N’-diacetylhydrazine with 1,2-diAMinoethane and 1,3-diAMinopropane in methanol. The formation of macrocyclic ligand frAMeworks, the bonding of the macrocyclic moieties in the complexes and the overall geometry of the complexes were deduced based on the results obtained from elemental analyses as well as molar conductivity, FTIR, ¹H-, ¹³C-NMR, EPR, ESI-mass, UV–Vis spectral studies and magnetic measurements. An octahedral geometry is proposed for all the complexes, while a distortion in the octahedral geometry was registered for the Cu(II) complexes. Comparative fluorescence and UV–Vis studies on the Cu(II) complexes proved a significant binding to calf thymus DNA.

Keywords: octaazAMacrocycles; Cu(II), Co(II), Ni(II) and Zn(II) binuclear complexes; template condensation; DNA binding studies.

J. Serb. Chem. Soc. 74 (8–9) 953–964 (2009)

UDC 546.763+66.081+54–145.2:624.131.27; JSCS–3890; doi: 10.2298/JSC0909953B; Original scientific paper

Studies on chromium(III) removal from aqueous solutions by sorption on Sphagnum moss peat

CATALIN BALAN, DOINA BILBA and MATEI MACOVEANU

Department of Environmental Engineering and Management, Faculty of Chemical Engineering and Environmental Protection, Technical University of Iasi, D. Mangeron Blvd. 71A, 700050, Iasi, Romania

(Received 16 November, revised 13 April 2009)

Batch sorption experiments were performed for the removal of chromium(III) ions from aqueous solutions using Romanian Sphagnum moss peat (untreated and treated with NaCl solution) as sorbent. In order to establish the best conditions for the sorption of chromium(III), the influence of initial pH, contact time, peat dose and metal ion concentration was investigated. The Freundlich, Langmuir and Dubinin–Radushkevich models were applied to describe the sorption isotherms and to calculate its constants. The experimental data fitted well to the Langmuir model with a maximum sorption capacity of 18.6 mg Cr(III)/g of peat. The mean free energy of sorption suggests that the binding of Cr(III) on peat occurred through an ion exchange mechanism. The kinetic data evaluated by pseudo-first order and pseudo-second order kinetic models showed that the sorption of chromium onto the peat followed a pseudo-second order rate equation. The chromium(III) could be easily eluted from the loaded peat using 0.10 M HCl and the peat may be reused in several sorption/desorption cycles. The experimental results indicated the potential of Sphagnum moss peat for removal of Cr(III) from wastewaters.

Keywords: Sphagnum moss peat; Cr(III), sorption; equilibrium studies; kinetics.

J. Serb. Chem. Soc. 74 (8–9) 965–975 (2009)

UDC 546.923’962+544.478:66.087.3; JSCS–3891; doi: 10.2298/JSC0909965P; Original scientific paper

Activity of carbon supported Pt₃Ru₂ nanocatalyst in CO oxidation

KSENIJA DJ. POPOVIĆ, JELENA D. LOVIĆ, AMALIJA V. TRIPKOVIĆ and PIOTR K. OLSZEWSKI*

ICTM – Institute of Electrochemistry, University of Belgrade, Njegoševa 12, P.O. Box 473, 11000 Belgrade, Serbia

*Institute of Catalysis and Surface Chemistry, Polish Academy of Sciences, Krakow, Niezapominajek 8, 30-239, Poland

(Received 23 February, revised 24 April 2009)

The electrocatalytic activity of Pt₃Ru₂/C nanocatalyst toward the electro-oxidation of bulk CO was exAMined in acid and alkaline solution at AMbient temperature using the thin-film, rotating disk electrode (RDE) method. The catalyst was characterized by XRD analysis. The XRD pattern revealed that the Pt₃Ru₂/C catalyst consisted of two structures, i.e., Pt–Ru-fcc and Ru-hcp (a solid solution of Ru in Pt and a small AMount of Ru or a solid solution of Pt in Ru). Electrocatalytic activities were measured by applying potentiodynAMic and steady state techniques. The oxidation of CO on the Pt₃Ru₂/C catalyst was influenced by pH and anions from the supporting electrolytes. The Pt₃Ru₂/C was more active in alkaline than in acid solution, as well as in perchloric than in sulfuric acid. Comparison of CO oxidation on Pt₃Ru₂/C and Pt/C revealed that the Pt₃Ru₂/C was more active than Pt/C in acid solution, while both catalysts had a similar activity in alkaline solution.

Keywords: CO oxidation; Pt3Ru2/C nanocatalyst; XRD; pH effect; anion effect.

J. Serb. Chem. Soc. 74 (8–9) 977–984 (2009)

UDC 546.873+543.23+543.4/.5+542.97; JSCS–3892; doi: 10.2298/JSC0909977R; Short communication

SHORT COMMUNICATION

Kinetic spectrophotometric determination of Bi(III) based on its catalytic effect on the oxidation of phenylfluorone by hydrogen peroxide

SOFIJA M. RANČIĆ and SNEŽANA D. NIKOLIĆ-MANDIĆ*

Faculty of Science, Department of Chemistry, University of Niš, Višegradska 33, 18000 Niš, Serbia

*Faculty of Chemistry, University of Belgrade, Studentski trg 16–22, 11000 Belgrade, Serbia

(Received 1 December 2008, revised 15 April 2009)

A new reaction was suggested and a new kinetic method was elaborated for determination of Bi(III) in solution, based on its catalytic effect on the oxidation of phenyl-fluorone (PF) by hydrogen peroxide in AMmonia buffer. By application of spectrophotometric technique, a limit of quantification (LQ) of 128 ng cm^-3 was reached, and the limit of detection (LD) of 37 ng cm^-3 was obtained, where LQ was defined as the ratio signal:noise = 10:1 and LD was defined as signal 3:1 against the blank. The RSD value was found to be in the range 2.8–4.8 % for the investigated concentration range of Bi(III). The influence of some ions upon the reaction rate was tested. The method was confirmed by determining Bi(III) in a stomach ulcer drug (“Bicit HP”, Hemofarm A.D.). The obtained results were compared to those obtained by AAS and good agreement of results was obtained.

Keywords: kinetic method; catalytic reaction; Bi(III) determination.

J. Serb. Chem. Soc. 74 (8–9) 985–992 (2009)

UDC 546.173+542.97+543.4/.5:628(083.76); JSCS–3893; doi: 10.2298/JSC0909985M; Short communication

SHORT COMMUNICATION

Spectrophotometric determination of nitrite based on its catalytic effect on the reaction of nuclear fast red and potassium bromate

HASSAN ZAVVAR MOUSAVI and HAMID SHIRKHANLOO*

Chemistry Department, College of Sciences, Semnan University, Semnan.Iran

*Research Institute of Petroleum Industry, Medical Industrial Laboratory, Tehran, Iran

(Received 16 January, revised 24 April 2009)

A highly selective and sensitive catalytic spectrophotometric method was developed for the determination of nitrite in water sAMples. The method is based on its catalytic effect on the nuclear fast red–potassium bromate redox reaction in acidic medium. The reaction was followed spectrophotometrically by measuring the change in the absorbance at 518 nm of nuclear fast red 5 min after initiation of the reaction. In this study, the experimental parAMeters were optimized and the effects of other cations and anions on the determination of nitrite were exAMined. The calibration graph was linear in the range 2.0–45 µg mL^-1 of nitrite. The relative standard deviations for the determination of 15 and 30 µg mL^-1 of nitrite were 3.1 and 1.75 %, respectively (n = 8). The detection limit calculated from three times the standard deviation of the blank 3S_b was 0.7 µg mL^-1. The method was successfully applied to the determination of nitrite in spiked tap, natural and wastewater sAMples.

Keywords: nitrite; catalytic reaction; spectrophotometric; nuclear fast red.

J. Serb. Chem. Soc. 74 (8–9) 993–1007 (2009)

UDC 665.75.000.57+66.095.13/.14:665.2.000.68; JSCS–3894; doi: 10.2298/JSC0909993P; Original scientific paper

Alkali-catalyzed production of biodiesel from waste frying oils

ZLATICA J. PREDOJEVIĆ and BILJANA D. ŠKRBIĆ

Faculty of Technology, University of Novi Sad, Bulevar cara Lazara 1, 21000 Novi Sad, Serbia

(Received 18 February, revised 8 April 2009)

The effects of the transesterification parAMeters on the yield and quality of the methyl esters (MEs) produced from waste frying oil (WFO) were investigated. A two-step alkali transesterification reaction followed by silica gel purification step was applied. The investigated reaction parAMeters were the methanol/oil molar ratio (6:1 and 9:1), the catalyst/oil weight ratio (1.0 and 1.5 mass %) and the type of catalyst (NaOH and KOH). The physical and chemical properties of the employed feedstock and the obtained biodiesel were determined in order to investigate the effects of both the properties of the WFO and the reaction parAMeters on the characteristics and yields of the product. It was found that the properties of the feedstock had a determinant effect on the physical and chemical properties of the MEs, as the majority of them did not differ significantly under the studied reaction parAMeters. However, the reaction parAMeters influenced the yields of the product. Higher yields were obtained with a 1.0 than with a 1.5 mass % catalyst to oil ratio. The increasing yield with decreasing catalyst/oil ratio was more pronounced with NaOH (9.15–14.35 %) than with KOH (2.84–6.45 %). When KOH was used as the catalyst, the yields were always higher (the mean yield was 94.86 %) in comparison to those obtained with NaOH (the mean was 84.28 %). Furthermore, the efficiency of KOH in conversion of WFO to purified MEs in comparison to NaOH was even more pronounced in the case of the higher methanol/oil ratio, i.e., for the 9:1 methanol/oil ratio, the yield increase with KOH was about 2 times higher than the yield with NaOH, regardless of the applied catalyst/oil ratio.

Keywords: biodiesel; waste frying oil; alkaline two-step transesterification.

J. Serb. Chem. Soc. 74 (8–9) 1009–1017 (2009)

UDC 631.42:633.15+546.74; JSCS–3895; doi: 10.2298/JSC0909009Z; Original scientific paper

The effects of some agrotechnical measures on the uptake of nickel by maize plants

BRANKA M. ŽARKOVIĆ and SRDJAN D. BLAGOJEVIĆ

Faculty of Agriculture, University of Belgrade, Nemanjina 6, 11081, Belgrade, Serbia

(Received 21 January, revised 11 March 2009)

Nickel is a non-essential element in the nutrition of the majority of plant species and can be toxic to plants when its concentration in soils is high. Several soil properties have an effect on the uptake of this heavy metal by plants. The purpose of this investigation was to determine the effect of fertilization, soil acidification and liming on the uptake of Ni by maize plants grown on some alluvial soils. A pot experiment with maize plants grown on soils having various properties and elevated content of Ni was set up. The experiment lasted six weeks. The roots and shoots were analyzed for the concentration of Ni. From the results of the experiment, it can be concluded that the roots had higher concentrations of Ni than the shoots. The addition of mineral fertilizers (without application of other measures) mainly decreased the concentration and uptake of Ni by the roots and the transport of Ni to the shoots. Soil acidification (to pH 4.5) caused an increase in the Ni concentration in the plants and in its removal from the soil. Liming of acid soils had a positive effect on the uptake of Ni by young maize plants. The obtained results are important from the standpoint of reducing the pollution of plants by potentially toxic heavy metals.

Keywords: agrotechnical measures; Ni; uptake; concentration; maize.

J. Serb. Chem. Soc. 74 (8–9) 1019 (2009)

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