J. Serb. Chem. Soc. 75 (5) 595–603 (2010)
UDC  547.295.2+547.288.2+542.913+547:616.032:611.778; JSCS–3990; doi: 10.2298/JSC090527034F; Original scientific paper

Esters and AMides of hexanoic acid substituted with tertiary AMino group in terminal position and their activity as transdermal permeation enhancers
OLDŘICH FARSA, PAVEL DOLEŽAL* and ALEXANDR HRABÁLEK**

Institute of Chemical Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackého 1/3, 612 42 Brno, Czech Republic

*Department of Pharmaceutical Technology, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic

**Department of Inorganic and Organic Chemistry, Faculty of Pharmacy, Charles University, Hradec Králové, Czech Republic

(Received 27 May 2009, revised 4 January 2010)

Series of alkyl esters of 6-(diethylAMino)-, 6-(pyrrolidin-1-yl)-, 6-(pi¬peridin-1-yl) and 6-(morpholin-4-yl)hexanoic acids and alkylAMides of 6-(dimethylAMino)-, 6-(piperidin-1-yl) and 6-(morpholin-4-yl)hexanoic acids, containing 8–12 carbon atoms in the alkyl chain, were prepared by methods of classical organic synthesis. The appropriate secondary AMine was alkylated with ethyl 6-bromohexanoate to give ester of ω-substituted hexanoic acid, except of ethyl 6-(dimethylAMino)hexanoate (1), which was prepared by Eschweiler–Clarke methylation of 6-AMinohexanoic acid followed by direct esterification with ethanol. The resulted esters of ω-substituted hexanoic acids underwent direct transesterification with long chain alkanols to yield the desired AMino esters, or they were treated with long-chain alkylAMines to prepare secondary AMides of the appropriate heterocyclic hexanoic acids. These products were in vitro tested on their activity as transdermal permeation enhancers on the strips of the excised human skin with theophylline as the model permeant. The activity was evaluated using parAMeter enhancement ratio (ER), defined as the ratio between the overall AMount of the permeant passing through the skin with the tested enhancer and that without tested substance. Decyl 6-(pyrrolidin-1-yl)hexanoate (9) with ER = 30 showed the highest activity. The enhancing effects of the esters were generally better than those of the AMides.

Keywords: transdermal permeation enhancers; ω-AMino acid derivatives.

J. Serb. Chem. Soc. 75 (5) 605–614 (2010)
UDC 677.027.423.1/.2:535.683+535.685; JSCS–3991; doi: 10.2298/JSC090704039D; Original scientific paper

Synthesis, characterization and dyeing assessment of novel acid azo dyes and mordent acid azo dyes based on 2-hydroxy-4-methoxybenzophenone on wool and silk fabrics

BHARAT C. DIXIT, HITENDRA M. PATEL, RITU B. DIXIT* and DHIRUBHAI J. DESAI

Department of Chemistry, V. P. &AMp; R. P .T. P Science College, Vallabh Vidyanagar-388 120, Gujarat State, India

*Ashok &AMp; Rita Patel Institute of Integrated Study &AMp; Research in Biotechnology and Allied Sciences, New Vallabh Vidyanagar-388 120, Gujarat State, India

(Received 4 July 2009, revised 21 January 2010)

Novel acid mono azo and mordent acid mono azo dyes were synthesised by the coupling of diazonium salt solution of different aromatic AMines with 2-hydroxy-4-methoxybenzophenone. The resulting dyes were characterized by spectral techniques, i.e., elemental analysis, IR, ¹H-NMR and UV–visible spectroscopy. The dyeing performance of all the dyes was evaluated on wool and silk fabrics. The dyeing of chrome pre-treated wool and silk fabrics showed better hues on mordented fabrics. Dyeing of wool and silk fabrics resulted in pinkish blue to red shades with very good depth and levelness. The dyed fabrics showed excellent to very good light, washing, perspiration, sublimation and rubbing fastness. The results of antibacterial studies of chrome pre-treated fabrics revealed that the toxicity of mordented dyes against Escherichia coli, Staphylococcus aureus, Salmonella typhi, Bacillus subtilis bacteria was fairly good.

Keywords: acid azo dye; mordent acid azo dye; light fastness; washing fastness.

J. Serb. Chem. Soc. 75 (5) 615–627 (2010)
UDC 665+54–188:62–436.1; JSCS–3992; doi: 10.2298/JSC091008042S; Original scientific paper

Preparation of microcapsules containing different contents of different kinds of oils by a segregative coacervation method and their characterization

VERICA J. SOVILJ, JADRANKA L. MILANOVIĆ, JAROSLAV M. KATONA and LIDIJA B. PETROVIĆ

Faculty of Technology, Department of Applied and Engineering Chemistry, University of Novi Sad, Bul. cara Lazara 1, 21000 Novi Sad, Serbia

(Received 8 October, revised 17 December 2009)

Microencapsulation of different oils was performed using a segregative coacervation method. In order to microencapsulate, 20 % oil-in-water (O/W) emulsions were prepared in a continuous phase consisting of a 1 % mixture of hydroxypropylmethylcellulose (HPMC)/sodium carboxymethylcellulose (NaCMC) mass ratio (0.7/0.3) and various concentrations (0, 0.35 and 1 %) of the anionic surfactant sodium dodecylsulfate (SDS). Various interactions between the components occur in the continuous phase of emulsions, which influence the structure and properties of the adsorption layer around the oil droplets. The formed HPMC/SDS complexes in the presence of NaCMC molecules undergo segregative phase separation and form a coacervate which adsorbs onto the oil droplets, forming the wall of the microcapsules. Sunflower oil, pumpkin seed oil and a mixture of sunflower and linseed oil were used as the core material. Microcapsules in the solid form were obtained by spray drying the emulsions. The stability of the emulsions, the particle size and particle size distribution of the emulsions and suspensions of microcapsules and the oil content of the microcapsules were determined. The influence of the oil kind on the properties of the microcapsules was also investigated. It was found that at 0.35 % SDS, a coacervate layer around the oil droplets forms a stabile, compact microcapsules wall, which prevents oil extraction. The kind of oil influences the properties of the emulsions and microcapsules, which is important in the selection of oils for microencapsulation by this method.

Keywords: microencapsulation; coacervation; segregation; emulsions; oil content.

J. Serb. Chem. Soc. 75 (5) 629–637 (2010)
UDC 546.733’763’723’+542.9+547.571+547.511:615.28–188; JSCS–3993; doi: 10.2298/JSC090704037K; Original scientific paper

Synthesis, physical characterization and antimicrobial activity of trivalent metal Schiff base complexes
GAJENDRA KUMAR, DHARMENDRA KUMAR*, C. P. SINGH*, AMIT KUMAR and V. B. RANA

Department of Chemistry Meerut College, Meerut, (UP) 250001, India

*Department of Chemistry Sahu Jain College, Najibabad, (UP) 246763, India

(Received 19 June, revised 16 November 2009)

M(III) complexes of Cr, Mn and Fe with a Schiff base derived from 2-AMino-4-ethyl-5-hydroxybenzaldehyde and thiocarbohydrazide were synthesized and characterized by several techniques, including elemental analysis (C,H,N), molar conductance measurements, magnetic measurements, and electronic, mass and IR spectral studies. Based on these studies, a five-coordinated square pyrAMidal geometry for all the complexes was proposed. The Schiff base ligand and the complexes were also tested for their antimicrobial activity (against the bacteria Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Bacillus megaterium, and the fungi Kluyveromyces fragilis, Rhodotorula rubra, Candida albicans and Trichoderma reesei) to assess their inhibiting potential. An attempt was also made to correlate the antimicrobial activity with the geometry of the complexes. All complexes were found to be less active against the pathogens E. coli, S. aureus and P. aeruginosa. The Cr(III) complex showed the best antimicrobial activity, but the ligand alone was found to be active against the fungus T. reesei.

Keywords: Co (III), Cr (III) and Fe (III) complexes; Schiff Base; 2-AMino-4

-ethyl-5-hydroxybenzaldehyde; thiocarbohydrazide; antimicrobial activity.

J. Serb. Chem. Soc. 75 (5) 639–648 (2010)
UDC 547.53’788+547.235:546.562’742’472; JSCS–3994; doi: 10.2298/JSC090816040K; Original scientific paper

Benzothiazolylazo derivatives of some β-dicarbonyl compounds and their Cu(II), Ni(II) and Zn(II) complexes
KRISHNANNAIR KRISHNANKUTTY, MUHAMMED BASHEER UMMATHUR* and DAMODARAN KAMALAKSHY BABU**

Department of Chemistry, University of Calicut, Kerala-673635, India

*Department of Chemistry, Unity Women’s College, Manjeri, Kerala-676122, India

**Department of Chemistry, ZAMorin’s Guruvayurappan College, Calicut, Kerala-673014, India

(Received 16 August, revised 4 December 2009)

The coupling of diazotized 2-AMinobenzothiazole with 1,3-dicar-bonyl compounds (benzoylacetone, methyl acetoacetate and acetoacetanilide) yielded a new series of tridentate ligand systems (HL). Analytical, IR, ¹H--NMR, ¹³C-NMR and mass spectral data indicated that the compounds exist in the intrAMolecularly hydrogen bonded azo-enol tautomeric form in which one of the carbonyl groups of the dicarbonyl moiety had enolised and hydrogen bonded to one of the azo nitrogen atoms. The compounds formed stable complexes with Ni(II), Cu(II) and Zn(II) ions. The Cu(II) complexes conform to [CuL(OAc)] stoichiometry while the Ni(II) and Zn(II) complexes are in agreement with [ML₂] stoichiometry. Analytical, IR, 1H-NMR, ¹³C-NMR and mass spectral data of the complexes are consistent with the replacement of the chelated enol proton of the ligand with a metal ion, thus leading to a stable six-membered chelate ring involving a cyclic nitrogen, one of the azo nitrogens and the enolate oxygen. The Zn(II) chelates are diAMagnetic while Cu(II) and Ni(II) complexes showed a normal parAMagnetic moment.

Keywords: benzothiazolylazo-β-dicarbonyls; azo-enol form; Cu(II), Ni(II) and Zn(II) complexes; IR, mass and NMR spectral studies.

J. Serb. Chem. Soc. 75 (5) 649–657 (2010)

J. Serb. Chem. Soc. 75 (5) 659–667 (2010)

UDC 546.57.027:534.1/.2:539.2; JSCS–3996; doi: 10.2298/JSC090608035A; Original scientific paper

J. Serb. Chem. Soc. 75 (5) 669–679 (2010)

UDC 546.73’74’48’47+66–914.7:547.652:543.421; JSCS–3997; doi: 10.2298/JSC090404032M; Original scientific paper

J. Serb. Chem. Soc. 75 (5) 681–687 (2010)

UDC 632.95+546.185+541.135.5–039.26+543.552; JSCS–3998; doi: 10.2298/JSC090624033P; Short communication

SHORT COMMUNICATION

VoltAMmetric determination of the neonicotinoid insecticide thiAMethoxAM using a tricresyl phosphate-based carbon paste electrode

ZSIGMOND J. PAPP, VALÉRIA J. GUZSVÁNY, SZYMON KUBIAK*, ANDRZEJ BOBROWSKI* and LUKA J. BJELICA

Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of  Novi Sad, Trg D. Obradovića 3, 21000 Novi Sad, Serbia

*Department of Building Materials Technology, Faculty of Materials Science and CerAMics, AGH-University of Science and Technology, Mickiewicza 30, 30-059 Krakow, Poland

(Received 24 June, revised 26 November 2009)

The objective of the work was to investigate the possibility of using a tricresyl phosphate-based carbon paste electrode for the direct voltAMmetric determination of the neonicotinoid insecticide thiAMethoxAM. The analyte was determined by differential pulse voltAMmetry in Britton–Robinson buffer pH 7.0 in the concentration range of 3.72–41.5 µg mL^-1. The reproducibility of the analytical signal at the 7.29 µg mL^-1 level was characterized by a relative standard deviation of 1.3 %. The applicability of the developed method was evaluated by determining thiAMethoxAM in a river water sAMple and a commercial formulation Actara 25 WG.

Keywords: pesticide; thiAMethoxAM; differential pulse voltAMmetry; carbon paste electrode; tricresyl phosphate.

J. Serb. Chem. Soc. 75 (5) 689–701 (2010)

UDC 665.941+547.281+661.717.52–12:66.095.26:543.51; JSCS–3999, doi: 10.2298/JSC091030036G; Original scientific paper

Molar-mass distribution of urea–formaldehyde resins of different degrees of polymerisation by MALDI-TOF mass spectrometry

IVANA GAVRILOVIĆ-GRMUŠA, OLIVERA NEŠKOVIĆ*, MILANKA ĐIPOROVIĆ-MOMČILOVIĆ and MLAĐAN POPOVIĆ

Faculty of Forestry, University of Belgrade, Kneza Viseslava 1, 11030 Belgrade, Serbia

*Department of Physical Chemistry, Institute “Vinča” Belgrade, Mike Petrovića-Alasa 12–14, 11351 Belgrade, Serbia

(Received 30 October 2009, revised 25 January 2010)

This paper describes some results obtained in an investigation of urea–formaldehyde (UF) resins of different degrees of polymerisation by matrix-assisted laser desorption/ionisation time-of-flight (MALDI-TOF) mass spectrometry (MS). MALDI-TOF MS proved to be an appropriate technique for analyzing these types of polymers, bearing in mind that the results of the analysis correspond with previous physical and chemical measurements. This technique enables a relatively swift determination of the degree of polymerrisation through the monitoring of key changes in the structure of a polymer. Thus, in the analysis of UF resins, it may be possible to monitor a decrease in the intensity of the monohydroxymethyl urea (MMU) signal, which corresponds to an increase of the mass spectra values in the mass range of higher homologues, above 1000 g mol^-1. A noticeable difference concerns the signal intensities in the higher mass ranges (up to 1400 g mol^-1), which corresponds to more branched and longer homologues of the polymers. Especially, a significantly more intensive signal of MMU was registered. The average molecular weight (MW) of the exAMined sAMples was between 936 and 1324 g mol^-1, with a maximal deviation of 20 %, depending on the ratios of the reactants.

Keywords: urea-formaldehyde resins; molar ratio; molecular structure; degree of polymerisation; MALDI-TOF.

J. Serb. Chem. Soc. 75 (5) 703–715 (2010)

UDC 546.224–31+66–914:542.08+519.233(497.11Obrenovac); JSCS–4000; doi: 10.2298/JSC081026030N; Original scientific paper

Impacts of some meteorological parAMeters on the SO₂ concentrations in the City of Obrenovac, Serbia

SNEŽANA S. NENADOVIĆ, LJILJANA LJ. MATOVIĆ, MIŠKO M. MILANOVIĆ*, SAVA V. JANIĆEVIĆ**, JASMINA D. GRBOVIĆ NOVAKOVIĆ and MILUTIN A. LJEŠEVIĆ*

Vinča Institute, Laboratory of Materials Sciences, P.O. Box 522, 11000 Belgrade, Serbia

*Institute for Environmental Research and Geographic Information Systems, Studentski trg 3/III, 11000 Belgrade, Serbia

**Institute for Geography, Faculty of Natural Sciences and Mathematics, University of Novi Sad, Trg Dositeja Obradovića, 21000 Novi Sad, Serbia

(Received 21 October 2008, revised 12 November 2009)

In this paper, the impacts of some meteorological parAMeters on the SO2 concentrations in the City of Obrenovac are presented. The City of Obrenovac is located in the north-west part of Serbia on the banks of the River Sava. The observed source emission, the power plants TENT A and B are situated on the bank of the Sava River in the vicinity of Obrenovac. During the period from January to November 2006, the concentrations of sulfur dioxide in the air at 4 monitoring sites in Obrenovac were measured. It was noticed that the maximal measured daily concentrations of sulfur dioxide ranged from 1 μg m^-3 (16^th November, 2006) to 98 μg m^-3 (29^th January 2006) and lie under the maximal allowed concentration value according to the Serbian Law on Environmental Protection. The measured sulfur dioxide concentrations mostly showed characteristics usual for a daily acidification sulfur dioxide cycle, excluding the specificities influenced by the measuring site itself. Sulfur dioxide transport was recorded at increased wind speeds, primarily from the southeast direction. Based on the impact of meteorological parAMeters on the sulfur dioxide concentration, a validation of the monitoring sites was also performed from the aspect of their representivity.

Keywords: sulfur dioxide; correlation; meteorological data; thermal power plant; environment.

J. Serb. Chem. Soc. 75 (5) 717–732 (2010)

UDC 556.551+614.777/.778:504.45.058(497.11Palić); JSCS–4001; doi: 10.2298/JSC091016043G; Original scientific paper

The evolution of the trophic state of the Palić Lake (Serbia)

IVAN GRŽETIĆ and NATAŠA ČAMPRAG*

University of Belgrade, Faculty of Chemistry, Studentski trg 12–16, 11 000 Belgrade, Serbia

*Public Health Institute of Subotica, Zmaj Jovina 30, 24 000 Subotica, Serbia

(Received 16 October 2009, revised 12 November 2009)

The Palić Lake is a shallow lake typical for the Pannonian Plain. Due inadequate water quality, it was dried out in 1971 and re-established in 1977 and since than its trophicity has been worsening. Investigation of the long-term changes in the trophic state of this lake were tracked over the total phosphorous (TP), total nitrogen (TN), chlorophyll-a and Secchi disk transparency (SDT), expressed as the Carlson trophic state index (TSI). Regarding the TSI values, the water of the Palić Lake has been constantly evolving from eutrophic to hypereutrophic. TN/TP values < 10 indicate that nitrogen is the limiting factor for algal growth.

Keywords: shallow lake; lake trophicity; eco-chemical status; trophic state index; eutrophication.

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