Open Access Published by De Gruyter Open Access

Volume 8 Issue 5

October 2010

Issue of Open Chemistry

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Open Access September 5, 2010

Isomers in the chemistry of iron coordination compounds

Milan Melnik, Mária Kohútová

Page range: 965-991

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Abstract

The coordination chemistry of iron covers a wide field, as shown by a survey covering the crystallographic and structural data of almost one thousand and three hundred coordination complexes. About 6.7% of these complexes exist as isomers and are summarized in this review. Included are distortion (96.6%) and cis — trans (3.4%) isomers. These are discussed in terms of the coordination about the iron atom, bond length and interbond angles. Distortion isomers, differing only by degree of distortion in Fe-L, Fe-L-Fe and L-Fe-L parameters, are the most common. Iron is found in the oxidation states zero, +2 and +3 of which +3 is most common. The stereochemistry around iron centers are tetrahedral, five — coordinated (mostly trigonal — bipyramid) and six — coordinated. The most common ligands have O and N donor sites.

Open Access September 5, 2010

Nickel and palladium complexes of enolatefunctionalised N-heterocyclic carbenes

Saravanakumar Shanmuganathan, Olaf Kühl, Peter Jones, Joachim Heinicke

Page range: 992-998

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Abstract

The reaction of chloroethyltrimethylsilylether with 1-methylimidazole furnishes an ionic liquid that undergoes methanolysis to crystalline 2-hydroxyethylimidazolium chloride (crystal structure presented). Conversion to defined hydroxyethylimidazol-2-ylidene nickel complexes failed, but was accomplished with 1-methyl-3-acetophenyl-imidazolium bromide. The bis(NHC⋂O−) nickel(II) chelate is formed, rather than a methallylnickel monochelate, but with nickelocene a monochelate NiCp complex was detected. The bulky 1-(2,6-diisopropylphenyl)-3-(2’-phenyl-enolato)-imidazol-2-ylidene allylpalladium chloride was obtained in pure form. Attempts to generate catalysts for ethylene oligomerization by in situ techniques have failed so far whereas P⋂O− ligands, comparable by the P-C diagonal relationship, provide active catalysts.

Open Access September 5, 2010

Square wave anodic stripping voltammetry determination of eco-toxic metals in samples of biological and environmental importance

Zefi Anastasiadou, Panagiotis Jannakoudakis, Stella Girousi

Page range: 999-1008

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Abstract

Square wave anodic stripping voltammetry was used in simultaneous determinations of eco-toxic metals (Pb, Cd, Cu and Zn) on bismuth film electrodes. The electrodes were prepared in situ on a glassy-carbon electrode (GCE) from 0.1 M acetate buffer (pH 4.5) containing 200 μg L−1 of bismuth (III), as well ex situ on electrochemically oxidized graphitized polyacrylonitrile carbon fibres from 200 mg L−1 Bi(NO3)3 in 1% HNO3 (aqueous) solution. Preparation of a Bi-modified carbon fibre electrode (CFE) was by cation exchange of Bi+3 ions for H+ of the acidic surface groups of the electro-oxidized carbon fibres, followed by electrochemical reduction to Bi0. For the Bi-GCE the linear range was 20–280 μg L−1 for zinc, 10–100 μg L−1 for lead, 10–80 μg L−1 for copper, and 5–50 μg L−1 for cadmium. For the Bi-CFE it was 20–160 μg L−1 for zinc, 10–100 μg L−1 for lead, 10–100 μg L−1 for copper, and 2–120 μg L−1 for cadmium. For both kinds of bismuth modified carbon electrodes, low limits of detection and satisfactory precision were achieved. The method was successfully applied to certified reference materials of biological (bovine liver) and environmental (mussel tissue) importance.

Open Access September 5, 2010

Three-dimensional Monte Carlo simulations of the dynamics of macromolecular particles in solutions flowing in mesopores

Ali Atwi, Antoine Khater, Abbas Hijazi

Page range: 1009-1013

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Abstract

Numerical simulations are developed to calculate the dynamic equilibrium probability distribution functions (PDF) for macromolecular rod-like particles suspended in a fluid under hydrodynamic flow inside mesopores. The simulations take into account the effects of Brownian and hydrodynamic forces acting on the particles, as well as diffusive collisions of the particles with the solid surface boundaries. An algorithm is developed for this purpose based on Jeffery’s equations for the dynamics of ellipsoidal objects in bulk fluids, and on a mechanism of restitution for the diffusive collisions. The results are presented with a focus on the depletion layer next to two types of solid boundaries, ideally flat and rough. They demonstrate the significance of numerical simulations in 3D compared to previous results based on a 2D approach. In particular, we are able to obtain a complete topography for the PDFs segmented as a hierarchy in the depletion layer.

Open Access September 5, 2010

Toxic elements content in PM10 samples from a coastal area of the Northern Adriatic Sea

Federico Cozzi, Gianpiero Adami, Pierluigi Barbieri, Edoardo Reisenhofer, Pietro Apostoli, Massimo Bovenzi

Page range: 1014-1026

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Abstract

PM10 samples were collected during winter and summer seasons at two different sites in the area of Trieste (Italy). The content of As, Cd, Cr, Mn, Ni, Pb and V in the PM10 samples was determined by inductively coupled plasma-mass spectrometry, with the purpose of evaluating the relevance of PM10 inhalation as a route of human exposure to these elements. The results showed that the ambient air concentration of the aforementioned elements were below the limits or target values for both sites and season. Site and season-specific correlation analysis was conducted for the identification of metals with similar origin: very good correlation for the couple Ni-V was found in both sites and seasons, showing the influence of combustion of heavy oils in PM10 composition. The inter-site and seasonal variability of both PM10 and metal concentrations were examined. A stronger impact by the vehicular traffic on the PM10 and metal concentrations was found for the urban site in both seasons. Because of the great importance of the “Bora” wind on the local climate, variability of PM10 and toxic elements concentration with wind were analysed, allowing determination of the effect of wind on dilution of the pollutants for the urban site during both seasons.

Open Access September 5, 2010

Synthesis and optical properties of self-assembled flower-like CdS architectures by mixed solvothermal process

Junhao Zhang, Yuhui Wu, Jia Zhu, Shaoxing Huang, Dongjing Zhang, Qinghuan Yin

Page range: 1027-1033

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Abstract

Self-assembled CdS architectures with flower-like structures have been synthesized by a mixed solvothermal method using ethylene glycol and oleic acid as the mixed solvent at 160°C for 12 h. The results of X-ray diffraction (XRD) patterns, field-emission scanning electron microscopy (FESEM) and transmission electron microscopy (TEM) images indicate that the product exists as the hexagonal wurtzite phase and conatins of larger numbers of flower-like CdS architectures with diameters of 1.8–3 μm. The selected-area electron diffraction (SAED) pattern and the high resolution transmission electron microscope (HRTEM) image reveal that the grain has better crystallinity. The optical properties of flower-like CdS architectures were also investigated by ultraviolet-visable (UV-vis) and photoluminescence spectroscopy at room temperature. A strong peak at 490 nm is shown in the UV-vis absorption, while an emission at 486 nm and another strong emission at 712 nm are shown in the PL spectrum.

Open Access September 5, 2010

Screen-printed electrodes modified with HRP-zirconium alcoxide film for the development of a biosensor for acetaminophen detection

Veronica Sima, Cecilia Cristea, Ede Bodoki, Gabriela Duţu, Robert Sāndulescu

Page range: 1034-1040

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Abstract

The development of a biosensor based on the immobilization of horseradish peroxidase (HRP) within a zirconium alkoxide-polyetilenimine film onto screen-printed electrodes (SPE) for acetaminophen detection and acetaminophen quantification in pharmaceutical products is described. The biosensor operation mode is based on monitoring the amperometric signal produced by the electrochemical reduction of the enzymatically generated electroactive oxidized species of acetaminophen in the presence of hydrogen peroxide. The enzyme immobilization is performed by retention in a polyethylenimine-zirconium alcoxide porous gel film, a technique that offers good entrapping and a protective environment for the biocomponent due to the hydration properties of the immobilization layer. SPEs have the advantage of being easily mass-produced at low costs with superior characteristics in comparison with classical electrode materials. In this configuration, zirconium alkoxide demonstrates its electrocatalytic activity. The biosensor allows the quantification of acetaminophen with a limit of detection of 6.21×10−8 M and a linear range between 4.35×10−7 M and 4.98×10−6 M. Finally, the biosensor is applied to the quantitative analysis of acetaminophen in Perdolan® tablets.

Open Access September 5, 2010

Effect of the polymeric coating over Fe3O4 particles used for magnetic separation

Raúl Reza, Carlos Martínez Pérez, Claudia Rodríguez González, Humberto Romero, Perla García Casillas

Page range: 1041-1046

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Abstract

In this work, the synthesis of magnetite nanoparticles by two variant chemical coprecipitation methods that involve reflux and aging conditions was investigated. The influence of the synthesis conditions on particle size, morphology, magnetic properties and protein adsorption were studied. The synthesized magnetite nanoparticles showed a spherical shape with an average particle size directly influenced by the synthesis technique. Particles of average size 27 nm and 200 nm were obtained. When the coprecipitation method was used without reflux and aging, the smallest particles were obtained. Magnetite nanoparticles obtained from both methods exhibited a superparamagnetic behavior and their saturation magnetization was particle size dependent. Values of 67 and 78 emu g−1 were obtained for the 27 nm and 200 nm magnetite particles, respectively. The nanoparticles were coated with silica, aminosilane, and silica-aminosilane shell. The influence of the coating on protein absorption was studied using Bovine Serum Albumin (BSA) protein.

Open Access September 5, 2010

QSPR modelling of normal boiling points and octanol/water partition coefficient for acyclic and cyclic hydrocarbons using SMILES-based optimal descriptors

A.A. Toropov, A.P. Toropova, E. Benfenati

Page range: 1047-1052

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Abstract

Predictive quantitative structure - property relationships (QSPR) have been established for normal boiling points and octanol/water partition coefficient for acyclic and cyclic hydrocarbons using optimal descriptors calculated with simplified molecular input line entry system (SMILES). The probabilistic criteria for a rational definition of the domain of applicability of these models are discussed.

Open Access September 5, 2010

Removal of cadmium and copper ions by Trichosporon cutaneum R57 cells immobilized onto polyvinyl alcohol/tetraethoxysilane hybrid matrices

Rayna Bryaskova, Nelly Georgieva, Dimitar Peshev

Page range: 1053-1058

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Abstract

Polyvinyl alcohol (PVA) and tetraethoxysilane (TEOS) hybrid materials were prepared by sol-gel methods and tested as matrices for immobilization of Trichosporon cutaneum R57, capable of removing cadmium and copper ions from aqueous solutions. A kinetic model was applied and the effects of matrix TEOS content on the copper and cadmium uptake equilibria and rate constants were investigated.

Open Access September 5, 2010

Preparation and characterization of high specific surface area Mn3O4 from electrolytic manganese residue

Tiefeng Peng, Longjun Xu, Hongchong Chen

Page range: 1059-1068

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Abstract

Mn3O4 powders have been produced from Electrolytic Manganese Residue (EMR). After leaching of EMR in sulfuric acid, MnSO4 solution containing various ions was obtained. Purifying the solution obtained and then adding aqueous alkali to the purified MnSO4 solution, Mn(OH)2 was prepared. Two methods were employed to produce Mn3O4. One way was oxidation of Mn(OH)2 in aqueous phase under atmosphere pressure to obtain Mn3O4. The other way was roasting Mn(OH)2 precursors in the range of 500°C to 700°C. The prepared samples were investigated by using several techniques including X-ray powder diffraction (XRD), Fourier Transformation Infra-Red (FTIR) spectra, and Brunauer-Emmett-Teller (BET) specific surface area instrument. Particle distribution and magnetic measurements were carried out on laser particle size analyzer, vibrating sample magnetometer (VSM). Through XRD, FTIR and determination of total Mn content (TMC), the products prepared were confirmed to be a single phase Mn3O4. BET specific surface areas can reach to 32 m2 g−1. The results indicated that products synthesized by aqueous solution oxidation method had higher specific surface areas and smaller particle size than those prepared by means of roasting. However the products prepared using the above two methods showed no obvious differences in magnetic property.

Open Access September 5, 2010

Modeling and optimizing of sonochemical degradation of Basic Blue 41 via response surface methodology

Jalal Parsa, Mahmood Abbasi

Page range: 1069-1077

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Abstract

The nanocatalyst-assisted sonodegradation of Basic Blue 41 (BB41) dye in aqueous medium was modeled and optimized using response surface method (RSM) based on Box-Behnken design. The studied variables included pH, initial dye concentration, H2O2 concentration and sonolysis time while each factor varied at three levels: Low level (−1), Medium level (0) and High level (+1). The ultrasound -assisted degradation was well described by developing quadratic model with correlation value squared (R2) of 0.9114. Factor effects along with interaction effects were evaluated. The graphical optimization step was conducted to achieve the best experimental condition in dye removal. pH, H2O2 concentration and initial dye concentration of the reaction were investigated. It was recognized that at lower pH values the dye removal rate decreased. However, dye removal rate increased (82.5%) by increasing the concentration of H2O2 and by lowering the initial dye concentration.

Open Access September 5, 2010

Conductometric studies on the stability of copper complexes with different oligosaccharides

Ivan Savic, Goran Nikolic, Ivana Savic, Milorad Cakic

Page range: 1078-1085

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Abstract

Bioactive copper complexes with pullulan or dextran oligosaccharides are the subject of intensive research mainly because of their possible application in veterinary and human medicine. The thermal stability and stability under oxidative conditions of the Cu(II) complexes with reduced low-molar pullulan or dextran were investigated in this paper, using a conductometric method. The influence of ligand constitutions on the stability of the complexes was examined on the basis of ligand property. Forced degradation studies were performed on bulk sample of complexes by using heat (25, 40 and 60°C) and an oxidation agent (0.1, 0.5, 1.0 and 10.0% v/v hydrogen peroxide). It can be concluded, according to the results obtained (by examining conductivity during the forced degradation studies), that Cu(II) complexes show a large pharmaceutical stability for both tests.

Open Access September 5, 2010

Efficient and solvent-free synthesis of 1-amidoalkyl-2-naphthols using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide

Ramin Ghorbani-Vaghei, Seyedeh Malaekehpour

Page range: 1086-1089

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Abstract

N,N,N,’N’-Tetrabromobenzene-1,3-disulfonamide [TBBDA] is found to be a reusable catalyst for efficient synthesis of various amidoalkyl naphthols from β-naphthol, aromatic aldehydes and urea in good to high yields under solvent-free conditions.

Open Access September 5, 2010

Thermal stability and electrochemical behaviour of Tetrakis-μ-benzoatodicopper(II)

Mohammad Mohamadin, Norbani Abdullah

Page range: 1090-1096

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Abstract

Copper(II) benzoate (CuB) was synthesized and structurally characterized to have a binuclear, paddle-wheel structure. The complex was found to be thermally stable up to 230°C, and underwent four stages of decomposition, loss of CO2, C6H6, CH3CH2-OCH2CH3 and some aliphatic unsaturated organic materials. The DSC curve shows two endotherms at 80.0°C and 230.0°C respectively, indicating that the initial weight loss can be attributed to solvated molecules and the starting of the major decomposition process, (shown in the TG analysis). Cyclic voltammetry studies in a mixed-solvent system of methanol and ethanoic acid (20:1 v/v) show three cathodic peaks, at −0.13 V, −0.35 V and −0.74 V, representing a step-wise electron transfer process, and two overlapping anodic peaks at +0.31 V and +0.46 V. The high value of ΔE ranging from 400 mV to 1200 mV indicates that the redox process is accompanied by an extensive structural reorganization of the complex in the solution creating a different geometrical environment around the central copper ion.

Open Access September 5, 2010

NBO and NICS analysis of the allylic rearrangements (the Cope and 3-aza-Cope rearrangements) of hexa-1,5-diene and N-vinylprop-2-en-1-amine: A DFT study

Ehsan Zahedi, Safa Ali-Asgari, Vahid Keley

Page range: 1097-1104

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Abstract

In this work, ab initio density functional theory (DFT) calculations have been performed on the 3,3-sigmatropic rearrangements of hexa-1,5-diene (Cope) and N-vinylprop-2-en-1-amine (3-aza-Cope) in the gas phase. The barrier heights and heats of reactions calculated at the B3LYP/6-311G** level of theory were in good agreement with experimental data. Transition states optimized with B3LYP/6-311G** theory were used for calculating the nucleus independent chemical shift (NICS) and, a natural bond orbital (NBO) analysis was also performed at the same level of theory. Our results indicate that the aromaticities of the transition states are controlled by the out-of-plane component and that the chair-like transition state of the Cope rearrangement exhibits the strongest aromatic character. Analysis of donor-acceptor (bonding and anti-bonding) interactions of σ3–4 → π*1–2 suggests that the TS structure in the hexa-1,5-diene reaction (the Cope rearrangement) has more aromatic character than the N-vinylprop-2-en-1-amine reaction (the 3-aza-Cope rearrangement). The NBO results show that in the hexa-1,5-diene and N-vinylprop-2-en-1-amine rearrangements, activation energies are controlled by σ3–4 → π*1–2 and σ3–4 → π*1–2 resonance energies.

Open Access September 5, 2010

Characterization of sorption gels used for determination of mercury in aquatic environment by diffusive gradients in thin films technique

Pavel Diviš, Roman Szkandera, Hana Dočekalová

Page range: 1105-1109

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Abstract

The influence of pH, ionic strength and selected natural ligands on the measurement of mercury by the diffusive gradients in thin films technique (DGT) using recently introduced sorption gels was determined. Sorption gels containing Chelex 100, Spheron-Thiol, Duolite GT73 and modified Iontosorb AV resins were investigated, with the sorption capacity determined for all used sorption gels. The minimum DGT measurable concentrations were calculated from 3 times the standard deviation of mercury amount in unexposed sorption gels.

Open Access September 5, 2010

Separation and determination of tocopherols in vegetable oils by solid phase extraction on porous polymers SPE cartridges and capillary gas chromatography analysis

Mihail Beldean-Galea, Cristina Horga, Maria Coman

Page range: 1110-1116

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Abstract

In this study we present the solid phase extraction selectivity of tocopherols from vegetable oils using four porous polymers (Porapak P, Porapak Q, Porapak QS, Porapak N). The tocopherols elution from SPE cartridges was performed using several hexanes:ethyl acetate mixtures (100:0, 95:5, 90:10, 85:15, v/v). Tocopherols (α, γ and δ-tocopherol) were analyzed by gas chromatography without any derivation steep. The amount of NaOH used for triglyceride removal was optimized. Particularly liquid-liquid and solid phase extraction methods for the extraction of tocopherols from vegetable oils were compared. The results confirmed that porous polymers represent promising SPE alternatives for the extraction of tocopherols from oils.

Open Access September 5, 2010

Ab initio study of hydrogen bond complexes of ring compounds containing the H2N-C=Y moiety with water

Tao Liu, Guo-Dong Liu, Zhang-Yu Yu

Page range: 1117-1126

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Abstract

Ab initio calculations, including natural charge population and natural resonance theory analyses, have been carried out to study the two-way effects between hydrogen bonds (H-bonds) and the intramolecular resonance effect by using the H-bonded complexes of ring compounds containing the H2N-C=Y moiety (C=Y bond is contained in the six-membered or five-membered rings) with water as models. The amino groups in the four monomers of ring compounds (FAYs, Y represents the heavy atoms in the substituent groups, =CH, =N, =SiH, and =P, respectively) can all serve as H-bond donors (HD) and H-bond acceptors (HA) to form stable H-bonded complexes with water. The HD H-bond and resonance effect enhance each other (positive two-way effects) whereas the HA H-bond and resonance effect weaken each other (negative two-way effects). The resonance effect in FAY(1) (C=Y bond is contained in the six-membered rings) is weaker than that in formamide, and those in FAY(2) and FAY(3) (C=Y bonds are contained in the five-membered rings). The two-way effects between H-bond and resonance effect exist in the H-bonded complexes of ring compounds containing the H2N-C=Y moiety with water.

Open Access September 5, 2010

Synthesis, structural chemistry and antimicrobial activity of −(−) borneol derivative

Khalid Al-Farhan, Ismail Warad, Saud Al-Resayes, Moustafa Fouda, Mohamed Ghazzali

Page range: 1127-1133

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Abstract

Borneol is a monoterpene that is a part of traditional Chinese and Japanese medicine. (−) borneol reacted with methanesulfonyl chloride in THF/pyridine to afford the new 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate derivative in excellent yield. The product is characterized by H1NMR, C13NMR, mass spectroscopy as well as elemental analysis and its structure was identified by X-ray single crystal diffraction. The packing of 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methanesulfonate exhibits the non-classical C-H···O hydrogen bonding in C(4) and R22(8) chain and ring motifs as structural determinants. This was also confirmed by the analysis of Hirshfeld surfaces. The 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate antimicrobial activity was tested and compared with its parent (−) borneol against three different pathogens. Particularly, 1,7,7-trimethylbicyclo[2.2.1]hept-2-yl methane sulfonate showed high sensitivity, compared to Chloramphenicol reference material, against Escherichia coli.

Open Access September 5, 2010

Interfacial transfer of Cd2+ assisted by 4′ — morpholino-acetophenone-4-phenyl-3-thiosemicarbazone across the water/1,2-dichloroethane interface

Haluk Bingol, Tevfik Atalay

Page range: 1134-1139

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Abstract

The assisted transfer of heavy metal ions by interfacial complexation with 4′-morpholinoacetophenone-4-phenyl-3-thiosemicarbazone (MAPPT) at the interface between two immiscible electrolyte solutions (ITIES) was studied by cyclic voltammetry. The voltammograms obtained across the water/1,2-dichloroethane interface using the MAPPT ligand in the organic phase shows that the assisted metal ion transfers have different nature for different ions. The quasi-reversible voltammetric peak of the Cd2+ ion was obtained and is discussed in detail. The dependence of the half-wave transfer potential on MAPPT concentration showed that the equilibrium is effectively displaced towards a 1:3 (metal:ligand) stoichiometry with an association constant of log β o =15.46 (±0.11) for the Cd2+ ion, corresponding to the TIC/TID mechanism.

Open Access September 5, 2010

Ionic liquids - deanol derivatives as the Diels-Alder reaction solvents

Ewa Janus, Anna Syguda, Katarzyna Materna

Page range: 1140-1146

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Abstract

The Diels-Alder reaction between cyclopentadiene and dienophiles in deanol derivatives containing bis(trifluoromethylsulfonyl)imide anion as media have been studied. The effect of the substituents attached to the cation on the endo:exo selectivity as well as the reaction yield have been evaluated in the absence and presence of Lewis acid catalyst - Y(OTf)3. Catalytic activity of metal triflates and the recycling of chosen catalytic systems have also been investigated

About this journal

Open Chemistry is a peer-reviewed, open access journal that publishes original research, reviews, and communications in the fields of chemistry in an ongoing way. Our central goal is to provide a hub for researchers working across all subjects to present their discoveries, and to be a forum for the discussion of the important issues in the field.

There are no submission charges. In order to sustain the production of our fully-refereed open access journal, each article accepted for publication in Open Chemistry is subject to Article Processing Charges (APC).

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Advanced Nanomaterials for Energy, Environmental and Biological Applications
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Marine Environmental Sciences and significance of the multidiscplinary approaches for assessing pollutions, remedies, and predictions
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Energy conversion and energy storage reactions
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Recent Trends in Green Chemistry
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Therapeutic Potentials of Natural Compounds Targeting Malaria
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