Vol 88, No 4 (2018)
- Year: 2018
- Articles: 37
- URL: https://journals.rcsi.science/1070-3632/issue/view/13696
Article
Solubility of Copper(II) Chloride in Mixed Organic Oxygen-Containing Solvents
Abstract
Solubility of copper(II) chloride at 25°C in binary organic solvents consisting of dimethyl sulfoxide, N,N-dimethylacetamide, and 1,4-dioxane was determined by the isothermal saturation method. The shape of solubility isotherms for all ternary systems under study is connected with the structural type of formed copper chloride solvates, the composition of which is defined by the solvent donor number. Solvates crystallize predominantly, where the metal ion coordinates molecules of the solvent with a greater donor power. The temperature increase in the system CuCl2–dimethylacetamide–dioxane up to 50°C leads to the formation of the cluster compound [Cu4Cl6O(DMA)4]; its structure was determined by the X-ray structural analysis method.
Quantum Chemical Study of Niobium and Tantalum M4O10 Oxide Clusters and M4O10– Anions
Abstract
Structural parameters and vibrational frequencies of the clusters (Td)–Nb4O10, (C3v)-TaNb3O10, (D2d)-Nb4O10–, and (Cs)-TaNb3O10– were calculated. According to the (U)DFT/SDD calculations with BLYP, B3LYP, and PBE0 functionals magnetization of the anion (D2d)-Nb4O10– is distributed equally among four niobium atoms. In the anion (Cs)-TaNb3O10– unpaired electron presumably occupies niobium atoms. The distinction in contributions from Nb atoms in the magnetization of the tantalum-containing cluster grows with the exchange component of the DFT functional in the series of functionals BLYP < B3LYP < PBE0 < UHF.
Solvent Effect on the Rate of Thermal Decomposition of Diacyl Diperoxides
Abstract
The kinetics of thermal decomposition of didecanoyl diperoxyadipate in different organic solvents have been studied. The primary homolytic dissociation of the peroxide bond (O–O) is accompanied by secondary induced chain decomposition processes. The reaction medium affects both the rate of primary homolytic decomposition and secondary decomposition processes. Correlation equations have been proposed for the rate constants of the reactions under study and physicochemical parameters of the solvents.
Effect of Association on Nucleophilic Addition of (Meth)acrylic Aminoamides to Acrylic Acids in Aqueous Solutions
Abstract
Reactions of nucleophilic addition of N-(3-dimethylaminoalkyl)(meth)acrylamides to acrylic, N-acryloylaminoacetic, and 2-acrylamido-2-methylpropanesulfonic acid with the formation of betaines revealed an unusual dependence of the initial rate and equilibrium conversion on concentration of the reagents. The observed effects were explained by structural features of the reagents and the products.
Effect of Glycine and Monoethanolamine on the Stability and Reductive Activity of Thiourea Dioxide in Aqueous Solutions
Abstract
The effect of glycine and monoethanolamine on the stability and reductive activity of thiourea dioxide in the reaction with acid orange II dye was studied. It was found that, in contrast to glycine, introduction of additives of monoethanolamine into aqueous solution of thiourea dioxide substantially increases its reductive activity in alkaline solutions, although the stability of the thiourea dioxide monoethanol amine derivative in alkaline solutions is much lower than that of thiourea dioxide and the product of its reaction with glycine.
One-Pot Synthesis of N-Substituted Alkylaminocyclohexanols by the Addition of Electrophiles Formed in situ in the System Н2О2 + HBr (HCl)
Abstract
Highly selective one-pot synthesis of N-substituted aminocyclohexanols has been performed by hydroxyhalogenation of the corresponding cyclohexenes with electrophilic reagents formed in situ in the system Н2О2 + HHlg (Hlg = Cl, Br), with subsequent substitution of halogen atoms with amines. Some products were tested as antimicrobial additives to motor oils and cooling lubricants and showed high antibacterial and antifungal activity.
Amidation of Diamantane with Organic Nitriles and CBr4 Under the Action of Granulated Zeolite FeHY
Abstract
N-(1- and 4-diamantyl)amides have been synthesized by the reaction of diamantane with organic nitriles in the presence of CBr4 under the action of granulated zeolite FeHY. The optimal ratios of the catalyst, reagents and the conditions for preparation of 1-N-diamantylamides in high yield have been found.
Synthesis and Properties of Functional Derivatives of 2,6-Diisobornylphenol and 2-Isobornyl-6-(1-phenylethyl)phenol
Abstract
New isobornylphenol derivatives have been produced by introducing allyl, hydroxypropyl, and chloropropyl groups into the para-position of 2,6-diisobornylphenol and 2-isobornyl-6-(1-phenylethyl)phenol. The radical scavenging and antioxidant activity and the membrane-protective properties of the newly-obtained compounds in chemical and biological model systems were studied.
Synthesis and Antibacterial Activity of 9-Oxo-9,10-dihydroacridinecarboxylic Acids Esters Bearing a Triazole Fragment
Abstract
An effective method for the synthesis of new acridine-9(10H)-one (acridone) derivatives containing 1,2,3-triazole fragment was developed. A number of new triazole-containing compounds were synthesized from propargyl acridone acetate and their antimicrobial activity was studied.
A New Approach to the Synthesis of Functional Derivatives of 3-(4-Pyridinyl)-1H-indole and 4-(1H-Indol-3-yl)thieno[2,3-b]pyridine
Abstract
Sequential reaction of indole-3-carbaldehyde with cyanothioacetamide and KOH led to the formation of potassium 6-amino-4-(1H-indol-3-yl)-3,5-dicyanopyridine-2-thiolate. S-Alkylation of the latter afforded new functional derivatives of 3-(pyridine-4-yl)-1H-indole and 4-(1H-indol-3-yl)-thieno[2,3-b]pyridine.
A Convenient Approach to 2-Aminobenzo[b]chalcogenophenes Based on Copper-Catalyzed Transformation of 4-(2-Bromophenyl)-1,2,3-chalcogenodiazoles in the Presence of a Base and Amines
Abstract
The reactions of 4-(2-bromophenyl)-1,2,3-thia-and -selenadiazoles with amines in the presence of potassium carbonate and copper(I) iodide afforded 2-aminobenzo[b]chalcogenophenes. The corresponding thiaand selenamides, prepared by interaction of 4-(2-bromophenyl)-1,2,3-thia- and -selenadiazoles with amines in the absence of copper salt, were transformed into 2-aminobenzo[b]chalcogenophenes by the action of potassium carbonate and copper(I) iodide in DMF in different yields.
Catalytic Action of Water during Nucleophilic Substitution of Halogen in Hexachlorocyclotriphosphazatriene with Pyridine N-Oxide
Abstract
The data on the kinetics of the reaction between hexachlorocyclotriphosphazatriene (the phosphazene) with pyridine N-oxide in mixed organic solvents in the presence of water are presented. The reaction of the phosphazene with pyridine N-oxide leads to the formation of the onium salt. It has been found that water catalyzes this reaction, the catalytic action resulting from the solvation of the polar transition state due to the formation of the phosphazene complex with hydrogen bonding, thus facilitating the rupture of the phosphorus bond with the leaving anion.
Synthesis and Isomer Composition of 2-Polyfluoroalkoxy-1,3,2-dioxaphospholanes and -phosphinanes
Abstract
Polyfluoroalkanols readily reacted with 2-chloro-1,3,2-dioxaphospholanes and 2-chloro-1,3,2-dioxaphosphinanes in hexane in the presence of triethylamine (–10 to 25°C, 5 h) to give 2-polyfluoroalkoxy-1,3,2- dioxaphospholanes and 2-polyfluoroalkoxy-1,3,2-dioxaphosphinanes in 48–72% yield. The products were found to exist as mixtures of cis and trans isomers with the trans isomer predominating for the phospholanes and cis isomer predominating for the phosphinanes according to the 1H, 13C, 19F, and 31P NMR data.
Coupling of Bis(xylylisocyanide) Palladium(II) Complex with 1,2,4-Thiadiazole-5-amines
Abstract
The coupling of bis(xylylisocyanide) complex of Pd(II) with 1,2,4-thiadiazole-5-amines leads to the formation of an equilibrium mixture of the binuclear complexes. In each of the studied cases, one of the formed complexes is the kinetic product, and the other one is the thermodynamic product. The complexes which are thermodynamic products have been isolated in the pure form and characterized by means of high-resolution mass spectrometry, IR and NMR spectroscopy, and X-ray diffraction analysis. NMR study of the regioisomerization in a solution has revealed that the relative stability of the thermodynamic products in comparison with the kinetic ones is higher than for the corresponding regioisomers containing 1,3-thiazole or 1,3,4- thiadiazole fragment.
Thermodynamic and Kinetic Parameters of Cerium(IV) Complexes with Some Dicarboxylic Acids
Abstract
The thermodynamic and kinetic parameters of the cerium(IV) complexes formed in the initial stage of oxidation of dicarboxylic acids (H2L), like pentanedioic, butanedioic, propanedioic, and ethanedioic acids, by cerium(IV) sulfate were studied by the spectrophotometric and pH-potentiometric methods with the aid of integral kinetic methods at an ionic strength I = 2 mol/L within the pH range of–0.3–1.6 in a sulfuric acid medium and at temperature of 293.15 K. The composition of these complexes, the form of organic ligand existence therein, the thermodynamic parameters of their formation, and the kinetic parameters of their intramolecular redox decomposition were determined. Linear correlations between the found thermodynamic and kinetic parameters of the examined complexes [CeOHL]+ were obtained. The rate equation of the redox process occurring in the systems Ce4+–H2L was established and the corresponding reaction model was considered.
Functionalized Polynorbornenes with Oligoether Units and Luminophoric Iridium(III) Complexes in Side Chains. Synthesis, Photophysical, and Biological Properties
Abstract
Copolymers with oligoether units and luminophoric iridium(III) complexes in the side chains have been synthesized via metathesis polymerization. The copolymers containing different luminophoric iridium(III) complexes have exhibited strong green, blue-green, or red photoluminescence. The copolymers are soluble in water, forming micelles with average size 14‒20 nm. The copolymer with red photoluminescence has low cytotoxicity with respect to epidermoid human carcinoma cells (line A431).
Synthesis and Properties of Tetra(4-tert-butyl-5-phenylsulfanyl)phthalocyanines and Their Derivatives
Abstract
The methods of synthesis of 4-tert-butyl-5-sulfanylphenyl-and 4-tert-butyl-5-(4'-carboxyphenylsulfanyl) phthalonitriles have been developed and on their basis the corresponding octa-substituted phthalocyanines have been prepared. The effect of the structure of the above phthalocyanine derivatives on their electronic absorption spectra and parameters of thermal degradation in the presence of air oxygen were studied.
Synthesis and Properties of Tetra-4-{[(1,1'-biphenyl)-4-yl]oxy}phthalocyanines and Their Sulfonic Acid Derivatives
Abstract
The template condensation of 4-{[(1,1'-biphenyl)-4-yl]oxy}phthalonitrile with cobalt, copper, and magnesium acetate resulted in the synthesis of metal phthalocyanines. Sulfochlorination of the latter followed by hydrolysis gave the corresponding sulfonic acid derivatives. The spectral characteristics and chemical properties of the synthesized compounds were studied.
Nucleophilic Substitution in 4-Bromo-5-nitrophthalodinitrile: XVI.1 4-(1H-Benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy/sulfanyl]- phthalonitriles and Cobalt Phthalocyanines Thereof
Abstract
A method of synthesis of 4-(1H-benzotriazol-1-yl)-5-[(4-carboxyphenyl)oxy]- and -5-[(4-carboxyphenyl) sulfanyl]phthalonitriles starting with 4-bromo-5-nitrophthalonitriles was developed. The synthesized phthalonitriles were used to prepare cobalt tetra-4-(1H-benzotriazol-1-yl)-tetra-5-[(4-carboxyphenyl)oxy/sulfanyl]phthalocyanines. The spectral and catalytic properties of the resulting octasubstituted phthalocyanines were studied.
Highly Efficiently Synthesis of Disubstituted Pyrrole Derivatives via Rh(III)-Catalyzed Direct C–H Alkylation Under Mild Conditions
Abstract
A mild and highly efficient Rh(III)-catalyzed direct C–H alkylation of pyrroles with diazo compounds has been developed. This green and atom-economic catalytic process enables an efficient access to various densely functionalized pyrrole derivatives in good to excellent yields, and it is potentially applicable to the large-scale synthesis of pyrrole derivatives.
Physicochemical and Biological Studies on Xipamide and Some of Its Complexes
Abstract
The new complexes of xipamide (XPD) with Ti(III), Ni(II), Pd(II), Zr(IV), Ce(IV), and U(VI) have been synthesized. Elemental analysis, magnetic properties, molar conductivities, thermal analysis, and UV-Vis, IR and 1H NMR spectra, elucidated the structures of complexes. According to spectral data, xipamide behaved in the obtained complexes as a bidentate chelating anion with the charge (–1) and coordinated via oxygen atoms of the deprotonated phenolic and carbonyl groups. Kinetic parameters of thermogravimetric analysys and its differential have been evaluated by using the Coats–Redfern and Horowitz–Metzeger methods. Thermodynamic data indicated thermal stability of all complexes. The ligand and its metal complexes were screened for their antifungal activity against A. fumigatus,G. candidum, syncephalastrum, and C. albicans, and antibacterial activities against two Gram-positive bacteria species, such as S. aureus and B. subtilis, two Gramnegative such as E. coli and P. aeruginosa.
Synthesis, Antimicrobial Activity, and Docking Studies of 2-Mercapto Substituted Quinazolin-4(3H)-one and Their Derivatives
Abstract
An efficient, eco-friendly synthesis of a series of 2-{[3-oxo-3-(alkyl/aryl-1-yl)alkyl]thio}-3-substituted quinazolin-4(3H)-ones employing quinazolin-4(3H)-one and corresponding halo-acyl/haloalkyl as electrophiles is presented. The products were assayed for anti-bacterial activity on four bacterial species (Pseudomonas aeruginosa, Escherichia coli, Bacillus subtilis, and Staphylococcus aureus). In-silico molecular docking studies were carried out.
An Efficient Microwave-Assisted Synthesis of Novel 2-{4-[(3-Aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones and Their Antimicrobial Activity
Abstract
The Buchwald–Hartwig amination reaction between 2-chloro-3-aryl-1,8-naphthyridines and 2-(4-aminophenyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione in the presence of the catalytic system Pd(PPh3)4 and the base KO-t-Bu in toluene was studied. The reaction was initiated by microwave irradiation. Highly efficient synthesis has been developed for 2-{4-[(3-aryl-1,8-naphthyridin-2-yl)amino]phenyl}-1H-benzo[de]isoquinoline-1,3(2H)-diones. Structures of the synthesized compounds were evaluated by IR, 1H and 13C NMR spectroscopy. All products were tested for antimicrobial activity against Escheria coli, Bacillus subtilis, Klebsiella pneumoniae, and Staphylococcus aureus.
Synthesis and Antibacterial Activity of Some {6-[(1H-1,2,3-Triazol-4-yl)methoxy]-3-methylbenzofuran-2-yl}(4-bromophenyl)methanone Derivatives
Abstract
A series of novel benzofuran−1,2,3-triazole hybrid heterocyclic molecules were synthesized using a click chemistry approach. The structure of the synthesized compounds was assessed by IR and NMR spectroscopy and mass spectrometry. The products showed moderate to high activity against gram-positive and gram-negative bacteria.
Preparation and Spectroscopic Studies of Charge-Transfer Complexes of Thiamine Hydrochloride with Different Electron Acceptor
Abstract
Abstract—Electronic interactions associated with charge transfer complexes formation of iodine, chloranilic acid (H2CA) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with vitamin B1 have been studied spectrophotometrically. The accumulated data indicated formation of CT-complexes of the general formula [(VB1)(acceptor)n], (n = 1 or 2). The 1 : 2 and 1 : 1 donor: acceptor molar ratios were calculated on the basis of elemental analysis and photometric titrations. The solid complexes were prepared and characterized by their conductivity, UV-Vis, IR, and 1H NMR spectra, and thermogravimetric analyses (TGA, DTG). The characteristic physical constants (KCT, εCT, μ, ΔG, Ip, f, ECT) of the formed CT-complexes were determined to be strongly dependent on nature of the electron acceptors.
Synthesis, Molecular Docking, Analgesic, and Anti-Inflammatory Activities of New 1,2,4-Oxadiazolo-Sulfonamides
Abstract
In the present study novel 1,2,4-oxadiazolo sulfonamides 3a–3o are synthesized by an efficient method based on the reaction of 1,2,4-oxadiazole amines with aryl sulfonyl chlorides. Structures of the synthesized compounds are confirmed by IR, NMR and Mass spectra. Molecular interactions of the obtained compounds are studied by Discovery Studio v3.5, molecular docking with COX-2 enzyme. The compounds with high LibDock score are screened for their in vivo analgesic and anti inflammatory activities. The compound 3l demonstrates the highest activity.
Synthesis and Antimicrobial Activity of 3-(1-Aryl-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)propan-1-ones
Abstract
A number of novel 3-(1-aryl-1H-1,2,3-triazol-4-yl)-2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl) propan-1-ones has been synthesized from 2-(4-fluorophenyl)-1-(2-hydroxy-4-methoxyphenyl)ethanone by its propargylation followed by the click reaction. Structures of all the newly synthesized compounds were characterized by 1H and 13C NMR, and Mass spectra. Their antimicrobial activity was evaluated.
Synthesis and Anti-H5N1 Activity of Substituted Pyridine Glycosides and (Oxadiazolyl)oxymethylpyridine Acyclic C-Nucleoside Analogues
Abstract
New aryl- and heteroaryl-substituted pyridinyl sugar hydrazones and their derivatives, 1,3,4-oxadiazole acyclic C-nucleosides, were synthesized. Novel O-glycoside derivatives of the substituted pyridines were prepared. The antiviral activity against avian influenza H5N1 virus was studied and compounds 5a, 9a, and 14 demonstrated high inhibition activity.
Letters to the Editor
Reaction of Styrene with Chlorine Dioxide
Abstract
Reaction of styrene with chlorine dioxide under various conditions selectively produces 1-phenyl- 2-chloroethanone, with 1-phenyl-2-chloroethanol, 2-hydroxy-1-phenylethanone, (1,2-dichloroethyl)benzene, (2-chloro-1-phenyl)ethene, and (1,2,2-trichloroethyl)benzene isolated as reaction byproducts.
Reaction of Amides of Sulfanyl, Thio-, and Carbonic Acids with Tropylium Salts
Abstract
By the reaction of urea, thiourea, sulfanilamide or sulfadimethoxine with tropylium tetrafluoroborate new products of substitution of hydrogen atom by the tropylium motif at the amide nitrogen atom or at the amino group of the benzene ring have been obtained.
Synthesis and Structure (Z)-N-Aryl-2-hydroxy-4-oxo-4-phenylbut-2-enamides
Abstract
Reactions of 5-phenyl-2,3-dihydrofuran-2,3-dione with aromatic amines in anhydrous dioxane or methyl benzoylpyruvate with aromatic amines in the presence of sodium acetate in glacial acetic acid afforded (Z)-N-aryl-2-hydroxy-4-oxo-4-phenylbut-2-enamides.
Arylation of Pyridine with 9,10-Dioxoanthracenyl-1(2)-diazonium Hydrosulfates
Abstract
9,10-Dioxoanthracenyl-1(2)-diazonium hydrosulfates reacted with pyridine under both the modified Gomberg–Bachmann reaction conditions and in the presence of catalytic amounts of CuCl2 to form a mixture of isomeric 2-, 3-, and 4-pyridylanthraquinones, of which 2-pyridyl derivatives were isolated in an analytically pure form.
Synthesis of New 1,4-Benzodioxanуl-1,2,4-triazole Derivatives
Abstract
The reaction of 5-(1,4-benzodioxan-2-yl)-4H-1,2,4-triazole-3-thiol with N-substituted chloroacetic acid amides obtained by condensation of chloroacetyl chloride with various primary amines furnished a series of S-amidomethyl derivatives. The corresponding thiazolotriazolone prepared from 2-[5-(1,4-benzodioxan-2-yl)-4H-1,2,4-triazol-3-ylthio]acetic acid reacted with aromatic aldehydes to form arylidene derivatives.
Synthesis and Structure of Zinc(II) Complexes with 2,2'-Bipyridine
Abstract
The structure of zinc(II) complexes with 2,2'-bipyridine obtained by a direct synthesis from multicomponent mixtures was studied by the method of X-ray structural analysis. The effects of the ligand environment on the composition of Zn|NxOy| coordination unit and on the nature of resulting polyhedra in the synthesized complex compounds were established.
Spectral Luminescent Properties of 3-[5-(4-Methoxyphenyl)-1,3,4-oxadiazol-2-yl]acrylic Acid and Its Complex with Zn(II)
Abstract
Zinc complex of (E)-3-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]acrylic acid has been prepared; its structure and composition have been elucidated by means of IR and 1Н as well as 13С NMR spectroscopy. Spectral luminescent properties of the ligand and the complex have been studied. Both compounds exhibit blueviolet luminescence (λmaxfl 402‒467 nm, φ 0.06–0.82) with low self-absorbance of the emitted light.