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Search results for: SYNTHESIS OF ALKYL GLYCOSIDES
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Micellar Route of the Synthesis of Alkyl Xylosides: An Unexpected Effect of Amphiphilic Imidazolium Ionic Liquids
PublicationThis manuscript presents results from the investigation on the synthesis of alkyl xylosides by the novel, very efficient and promising protocol of the Fischer synthesis from unprotected xylose and aliphatic alcohol. The use of 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids as the catalysts with dual functionality (surfactant + acid catalyst) and micellar reaction system are the main novelty of described method. It has...
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Antarctic, cold-adapted beta-galactosidase of Pseudoalteromonas sp. 22b as an effective tool for alkyl galactopyranosides synthesis
PublicationPrzedstawione jest zastosowanie arktycznej beta-galaktozydazy Pseudoalteromonas sp. 22b do katalizy syntezy alkilowych galaktopyranozydów. Njwyższą wydajność syntezy uzyskuje się przy pH 6-9 i 10-30% stężenia wody. Podobnie jak dla mezofilnych beta-galaktozydaz enzym antarktyczny syntetyzował najwydajniej kiedy reakcja przebiega w mieszaninie buforu i rozpuszczalnika organiczego (poniżej 50%, v/v).
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Cold-Active beta-Galactosidases: Sources, Biochemical Properties and Their Biotechnological Potential
Publicationbeta-D-Galactosidases have been studied extensively in terms of their application to a variety of industrial technologies. To date, considerable research efforts have been devoted to characterization of new cold-active beta-D-galactosidases which were isolated directly from selected species of bacteria and yeasts, as well as with the use of metagenomic approaches. This chapter will provide a review of current research towards cold-active...
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A novel cold-active β-D-galactosidase with transglycosylation activity from the Antarctic Arthrobacter sp. 32cB - gene cloning, purification and characterization
PublicationA gene encoding a novel β-D-galactosidase from the psychrotolerant Antarctic bacterium Arthrobacter sp. 32cB was isolated, cloned and expressed in Escherichia coli. The active form of recombinant β-D-galactosidase consists of two subunits with a combined molecular weight of approximately 257 kDa. The enzyme's maximum activity towards o-nitrophenyl-β-D-galactopyranoside was determined as occurring at 28 °C and pH 8.0. However, it...
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Sugar matters: sugar moieties as reactivity-tuning factors in quercetin O-glycosides
PublicationQuercetin, one of the most abundant flavonoids in plant-based foods, commonly occurs in nature in various glycosylated forms. There is still a less explored aspect regarding the cause of its glycosides diversity, depending on the sugars moiety attached. This work focuses on four widespread quercetin glycosides—hyperoside, isoquercitrin, quercitrin and rutin—by testing property-tuning capacity of different sugar moieties and thus...
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Membrane separation processes for the extraction and purification of steviol glycosides: an overview
PublicationSteviol glycosides (SGs), as natural sweeteners from Stevia rebaudiana, are currently employed for replacing sugar and its derivatives in several food products and formulations. Such compounds play an essential role in human health. Their usage provides a positive effect on preventing diseases related to sugar consumption, including diabetes mellitus, cancer, and lipid metabolism disorders. The traditional extraction of SGs is...
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N-Alkyl Derivatives of L-Glutamine As Inhibitors of Glutamine - Utilizing Enzymes
PublicationA general facile method to synthesize the N-gamma-alkyl and N-gamma,N-gamma-dialkyl derivatives of L-glutamine (1a-d) from L-glutamic acid as a starting substrate is presented. The obtained compounds are shown to inhibit three diferent glutamine-utilizing enzymes, namely: glutaminase, gamma-glutamyl transpeptidase, and glucosamine-6-phosphate synthase, with inhibitory constants within the milimolar range.
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Preparation of 1-[Ω-(1,4,5,6-Tetrahydropyrimidin-2-yl)alkyl]thymines
PublicationOne-stage prepn. of the hydrochloride salts of 1-[ω-(1,4,5,6-tetrahydropyrimidin-2-yl)alkyl]-thymines, e.g. I, from 1-(ω-cyanoalkyl)thymines and a 1:1-mixt. of 1,3-diaminopropane and ethanol satd. with hydrogen sulfide is described. 1-(2-Cyanoethyl)-thymine gave a facile reversal of the Michael reaction to thymine under the conditions used. The reaction of 1,3-bis(3-cyanobenzyl)thymine with the above reagent produced 1,3-bis[3-(1,4,5,6-tetrahydropyrimidin-2-yl)benzyl]thymine.
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Hydrolytical instability of hydroxyanthraquinone glycosides in pressurized liquid extraction
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Symmetrical and unsymmetrical diphosphanes with diversified alkyl, aryl and amino substituents
PublicationWe present the comprehensive study of diphosphanes with diversified substituents regarding their syntheses, structures, and properties. To this end, we have synthesized a series of novel unsymmetrical alkyl, aryl and amino-substituted diphosphanes of the general formula R1R2P-PR3R4 (where R1, R2, R3, R4 = tBu, Ph, Et2N or iPr2N) via salt metathesis reactionof halophosphanes with metal phosphides in high yield. We vastly expanded...
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Dual functionality of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids: surfactants with catalytic function
PublicationA series of amphiphilic 1-alkyl-3-methylimidazolium hydrogen sulfate ionic liquids were synthesized. Acidic hydrogen sulfate ionic liquids with the alkyl chains C6–C14 are characterized by good surface properties. Their surface properties (adsorption and micellization parameters, degree of ionization of micelles, Krafft temperatures and thermodynamic parameters) were determined. Synthesized ionic liquids were applied as a co-catalyst...
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Novel and Efficient Methods for the Synthesis of Symmetrical Trisulfides
PublicationWe have developed a convenient methods for the synthesis of symmetrical trisulfides under mild conditions in very good yields. The described methods are based on the straightforward preparation of 5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinane-2-disulfanyl derivatives from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The symmetrical...
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Apparent Molar Volumes and Expansivities of Ionic Liquids Based on N-Alkyl-N-methylmorpholinium Cations in Acetonitrile
PublicationDensities of some acetonitrile solutions of ionic liquids based on N-alkyl-N-methyl-morpholinium cations, N-ethyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide, N-butyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide, N-methyl-N-octylmorpholinium bis(trifluoromethanesulfonyl)imide and N-decyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide were measured at T = (298.15− 318.15) K and at atmospheric pressure....
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Thermal degradation of poly(alkyl methacrylates)
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A review of amide bond formation in microwave organic synthesis
PublicationMicrowave-Assisted Organic Synthesis (MAOS) is one of the most current trends in organic chemistry. Herein, both the most popular and new approaches in microwave-syntheses of very important linkage in Nature - amide bond - are overviewed and compared with conventional synthetic routes.
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Efficient Synthesis of Functionalized Unsymmetrical Dialkyl Trisulfanes
PublicationWe have developed a convenient method for the synthesis of functionalized unsymmetrical dialkyl trisulfanes under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with alkyl disulfanyl anions generated in situ from S-acetyl disulfanyl derivatives and sodium methoxide. The developed method allows for the preparation of...
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One-Step Synthesis of b-Lactams with Retro-Amide Side Chain
PublicationAbstract: A one pot synthesis for preparation of 1,4-disubstituted-2-oxo-azetidine-3-carboxylic acid amides was developed. 5-(α-N-substituted-amino-α'-hydroxy)methylene Meldrum's acids act as a source of ketenes that react with aldimines in boiling toluene to give b-lactams with retro-amid side chain.
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Beta-Galactosidases of Pseudoalteromonas sp. – Characteristics and application for lactose hydrolysis and galactopyranosides synthesis
PublicationBeta-galactosidase [EC 3.2.1.23] is an enzyme that catalyzes the hydrolysis of O-glycosidic linkages in galactosides. It has biotechnological applications in the dairy industry for the production of milk with a low content of lactose and galactooligosacharides for use in healthy food. The transgalactosylation activity of beta-galactosidase can be used in the synthesis of alkyl galactopyranosides. Due to the fact that conditions of...
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An efficient and convenient synthesis of unsymmetrical disulfides from thioacetates
PublicationWe have developed convenient methods for the synthesis of functionalized unsymmetrical dialkyl disulfides under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives 1 with functionalized alkyl thiolate anions, generated in situ from thioacetates2and sodium methoxide or butylamine. The developed method allows the preparation...
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Density, sound velocity, viscosity, and refractive index of new morpholinium ionic liquids with amino acid-based anions: Effect of temperature, alkyl chain length, and anion
PublicationIn this work, room temperature synthesis of twenty new ionic liquids (ILs) based on the N-alkyl-N-methylmorpholinium ([Mor1,R], R = 2, 3, 4, 6, 8) cation and N-acetyl-L-amino acid anions (L-alaninate, L-valinate, L-leucinate, L-isoleucinate) was described. The synthesized ILs were characterized by various spectroscopic techniques and high-resolution mass spectrometry. Furthermore, density (ρ), sound velocity (v), viscosity (η)...
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Solvation of ionic liquids based on N-methyl-N-alkyl morpholinium cations in dimethylsulfoxide – volumetric and compressibility studies
PublicationThe density and sound velocity of the solutions of ionic liquids based on N-alkyl-N-methyl-morpholinium cations, N-ethyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide, N-butyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide, N-methyl-N-octyl-morpholinium bis(trifluoromethanesulfonyl)imide and N-decyl-N-methylmorpholinium bis(trifluoromethanesulfonyl)imide in dimethylsulfoxide were measured at T = (298.15 to 318.15)...
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Comparison of Redox Properties of Flavonoid Aglycones and Corresponding Glycosides and Their Mixtures in the Cellular Model
PublicationFlavonoids are polyphenolic compounds commonly found in plants. As dietary components, they have been shown to exhibit numerous pro-health properties that are believed to be associated with their antioxidant effects. In this study, the antioxidant activity of four flavonoid compounds was determined by cellular antioxidant activity assay using HT29 cells as a model of the alimentary tract. The strongest impact on cellular redox...
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The Influence of Alkyl Chain Length and Steric Effect on the Stability Constants and Extractability of Co(II) Complexes with 1-Alkyl-2-Methylimidazoles
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Diastereoselective Synthesis of Z‐Alkenyl Disulfides from α‐Thiophosphorylated Ketones and Thiosulfonates
PublicationWe developed a simple and efficient method for the synthesis of functionalized unsymmetrical Z‐alkenyl disulfides under mild conditions in moderate to good yields. The designed method is based on the reaction of α‐thiophosphorylated carbonyl compounds with thiotosylates in the presence of a base. The developed method allows the preparation of unsymmetrical Z‐alkenyl disulfides bearing additional hydroxy, carboxy, or ester functionalities
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Determination of eight artificial sweeteners and common Stevia rebaudiana glycosides in non-alcoholic and alcoholic beverages by reversed-phase liquid chromatography coupled with tandem mass spectrometry.
PublicationThe method for the determination of acesulfame-K, saccharine, cyclamate, aspartame, sucralose, alitame, neohesperidin dihydrochalcone, neotame and five common steviol glycosides (rebaudioside A, rebaudioside C, steviol, steviolbioside and stevioside) in soft and alcoholic beverages was developed using high-performance liquid chromatography and tandem mass spectrometry with electrospray ionisation (HPLC-ESI-MS/MS). To the best of...
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Synthesis of malonylenamides and thiomalonylenamides
Publication5-[Hydroksyl(aryl(amino))methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione is convenient source of ketenes which can be trapped with various nucleophiles like alcohols, thiols and amines. In reaction between in situ generated ketene and enolizable imines we can easily obtain corresponding malonylenamides. This facile method can be used to obtain thiomalonylenamides using 5-[sulfhydrylo(alkyl(amino))methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione...
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Thermal degradation of copolymers based on selected alkyl methacrylates
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A novel and efficient synthesis of unsymmetrical disulfides
PublicationOpracowano metodę otrzymywania niesymetrycznych disulfidów z odpowiednich tioli w oparciu o bromek sulfenylowy.
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Two complementary approaches for the synthesis and isolation of stable phosphanylphosphaalkenes
PublicationPhospha-Wittig (phosphanylphosphinidene titanium(IV) complex) and phospha-Peterson (lithiated diphosphane) reactions were used to obtain phosphanylphosphaalkenes with the general formula XYC=P-PtBu2 (X = alkyl, aryl group or H; Y = alkyl or aryl group). Therefore, two series of reactions with different ketones and aldehydes were performed. An examination revealed that the two methods are complementary. For smaller carbonyl compounds,...
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Antimicrobial and surface activity of 1-alkyl-3-methylimidazolium derivatives
PublicationWiedza na temat zależności struktura-aktywność umożliwia projektowanie i syntezę nowych kationowych związków amfifilowych ze zoptymalizowaną aktywnością antymikrobową na rzecz przyszłego rozwoju nowych środków dezynfekujących, sanityzujących czy konserwujących. Potrzeba projektowania i identyfikowania nowych związków posiadających właściwości przeciwbakteryjne jest rezultatem pojawienia się bardziej odpornych mikroorganizmów w...
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Effect of alkyl sulfate on the phase behavior of microemulsions stabilized with monoacylglycerols
PublicationIn this study the effect of an anionic surfactant (sodium dodecyl sulfate SDS) and oils (hydrocarbons: C12-C16) on the formation and phase behavior of the systems of oil/monoacylglycerols (MAG):SDS/propylene glycol/water has been investigated. The effects of the surfactant mixture on the phase behavior and the concentrationof water or oil in the systems were studied at three temperatures (50, 55, 60 C). Electrical conductivity...
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A new and convenient method for the preparation of functionalized phosphorothioates
PublicationA new and efficient method for the synthesis of alkyl and aryl phosphorothioates in high yields via the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorin-2-yl)disulfanyl derivatives with trimethyl phosphite was developed.
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Practical Method for the Preparation of 2,2-Dimethyl-5- {aryl[(hetero)aryl]methyl}-1,3-dioxane-4,6-diones: Synthesis and Mechanistic Study
PublicationAn efficient practical synthetic procedure has been developed for the synthesis of 2,2-dimethyl-5-{aryl[(hetero)aryl]methyl}- 1,3-dioxane-4,6-diones through Friedel–Crafts alkylation. The scope and limitation of the reaction of 2,2-dimethyl-5-arylidene-1,3-dioxane- 4,6-diones with π-excess aromatic systems have been delineated.
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Novel and Efficient Methods for the Synthesis of Symmetrical Trisulfides
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Applications of Alkanethiols in Organic Synthesis
PublicationThis manuscript is an update to the earlier Science of Synthesis contribution describing methods for the synthesis of alkanethiols. Thiols can be converted into sulfonic, sulfinic, sulfenic acid and their derivatives, sulfides, disulfides, polysulfides, sulfonium salts, and thiiranes, etc. These transformations are accomplished by nucleophilic displacement or addition, oxidation, condensation, or coupling reactions involving thiol...
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Convenient and Efficient Synthesis of Functionalized 2-Sulfenylindoles
PublicationA simple, efficient, and practical sulfenylation at the C2 position of N-tosylindoles under mild conditions was developed. The designed transformation is based on the reaction of N-tosylindoles with BuLi and S-alkyl, and S-aryl phosphorodithioates or thiotosylates to produce 2-sulfenylindoles in moderate to high yields. The presence of additional hydroxy, carboxy, or amino functionalities did not disturb the formation of products
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Inhibition of impurities formation in the synthesis of N-alkyltheobromines stimulated by microwave irradiation. Cationic and anionic response of membrane electrodes
PublicationN-Alkyltheobromine (1-9) derivatives were obtained by reacting theobromine with appropriate alkyl halide under microwave irradiation at 100-150 W and by conventional synthesis. Formation of by-products of oxygen atom alkylation and 1-N-alkyltheobromine ring opening were considered. The presented compounds 1-5 have been studied as ion carriers in ion-selective membrane electrodes. Selectivity of these membranes was studied towards...
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S-thioacyldithiophosphates in the synthesis of thiohydroxamic acids and O-thioacylhydroxylamines
PublicationDitiofosforany tioacylu to trwałe, łatwo osiągalne z kwasów karboksylowych środki tioacylujące. Z powodu ich niskiej reaktywności wobec nukleofili tlenowych i wysokiej wobec nukleofili azotowych znalazły zastosowanie w syntezie kwasów tiohydroksamowych bezpośrednio z hydroksyloamin z niechronioną grupą hydroksylową. W przypadku dużej zawady przestrzennej można otrzymać O-tioacylohydroksyloaminy.
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Thermal degradation of poly(alkyl methacrylates) and polyurethane pressure-sensitive adhesives
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Amine–alkyl derivatives of hydantoin: New tool to combat resistant bacteria
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N-alkyl derivatives of 2-amino-2-deoxy-D-glucose
PublicationMono- i di-N-alkilowe pochodne 1,3,4,6-tetra-O-acetylo-2-amino-2-deoksy-beta-D-glukozy (alkil = metyl, etyl, propyl, butyl, pentyl, heksyl, benzyl) otrzymano w wyniku redukcyjnej alkilacji per-O-acetylo-D-glukozaminy. (N-etylo, N-propylo, N-butylo, N-pentylo, N-heksylo)-1,3,4,6-tetra-O-acetylo-2-amino-2-deoksy-beta-D-glukozy deacetylowano w celu podjęcia prób enzymatycznej fosforylacji. Wszystkie produkty scharakteryzowano za pomocą...
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The effect of alkyl chain length on synergistic effects in micellization and surface tension reduction in nonionic gemini (S-10) and anionic surfactants mixtures
PublicationMixtures of nonionic gemini surfactant S-10 ( α, α'-[2,4,7,9-tetrametyl-5-decyne-4,7-diyl]bis[ω-hydroxy -polioxyetylene] with anionic SRS (sodium alkylsulfates) and SRSO3 (sodium alkylsulfonates) of different alkyl chain length (from 10 to 14 carbon atoms) were investigated. Surface tension measurements were used to find the cmc values and other adsorption parameters. The Clint, Rubingh’s and Rosen theories were applied for evaluation...
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Microwave radiation in the synthesis of urethane prepolymers
PublicationThis paper describes the use of microwave radiation in the synthesis of urethane prepolymers in bulk (without solvent). The prepolymers were synthesized using 1,6-hexamethylene diisocyanate (HDI) and poly (ε-caprolactone) diol (PCL) at a molar ratio of 4:1. The reaction was carried out without a catalyst in the reactor with a conventional heating system (oil bath) or in the microwave reactor (MW Reactor NOVA 09) at temperatures...
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Impact of the Alkyl Side Chains of Cations and Anions on the Activity and Renaturation of Lysozyme: A Systematic Study Performed Using Six Amino‐Acid‐Based Ionic Liquids
PublicationThe impact of the structure of ionic liquid on the activity and renaturation of lysozyme from the hen egg white (HEWL) was investigated. A set of six ionic liquids based on morpholinium cation and N-acylated amino acids as anions were exploited. The matrix used was based on two homologous series: one with N-acetyl-L-valinate [Val] as a common anion and morpholinium cation with a different number of carbon atoms in the n-alkyl chain...
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Interactions of N-alkyl-N-methylmorpholinium based ionic liquids with acetonitrile studied by density and velocity of sound measurements and molecular dynamics simulations
PublicationMorpholinium-based ionic liquids (ILs) and their mixtures with polar co-solvents are an interesting class of emerging electrolytes in electrochemistry that is relatively poorly studied. In this work, densities and sound velocities of four ILs, N-ethyl-N-methylmorpholinium tetrafluoroborate, N-butyl-N-methylmorpholinium tetrafluoroborate, N-octyl-N-methylmorpho-linium tetrafluoroborate and N-decyl-N-methylmorpholinium tetrafluoroborate...
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Enhancement of ibuprofen solubility and skin permeation by conjugation with l-valine alkyl esters
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Alkyl Monolayers on Silicon Prepared from 1-Alkenes and Hydrogen-Terminated Silicon
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Thermal stability and degradation of selected poly(alkyl methacrylates) used in the polymer industry
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Chromogenic Azocrown Ethers with Peripheral Alkyl, Alkoxy, Hydroxyl or Di-methylamino Group.
PublicationOtrzymano nowe pochodne azobenzenowych eterów koronowych. Są to związki z grupą alkilową, alkoksylową, hydroksylową lub dimetyloaminową w reszcie (resztach) aromatycznej jako boczny podstawnik. Badano ich właściwości jako jonoforów w membranowych elektrodach jonoselektywnych oraz właściwości chromo-jonoforowe w roztworach. Badano kompleksowanie jonów metali, w acetonitrylu,przez te korony, metodą spektrofotometryczną. Badano...
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Recent Developments in the Synthesis of Unsymmetrical Disulfanes (Disulfides). A Review
PublicationThe synthesis of unsymmetrical disulfanes is an important transformation in organic synthesis and medicinal chemistry. The current review is intended to summarize achievements in the synthesis of unsymmetrical disulfanes over the last decade (2004–2014).