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Том 86, № 7 (2016)
- Жылы: 2016
- Мақалалар: 41
- URL: https://journals.rcsi.science/1070-3632/issue/view/13428
Article
Solubility of d-elements salts in organic and aqueous-organic solvents: III. Influence of intermolecular association on solubility of cadmium bromide and iodide
Аннотация
Solubility in the systems CdX2–H2O–Solv (X = Br, I; Solv = dimethyl sulfoxide, N,N-dimethyl acetamide, N,N-dimethyl formamide, and 1,4-dioxane) at 25°C was measured by the isothermal saturation method. A relation between the shape of the solubility isotherm and the structure of the binary solvent depending on its composition was found. Positions of solubility maxima and isotherms inflection points in the most cases correlate with destruction of intermolecular associates formed by solvent components.
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Synthesis and properties of double copper(I)–nickel(II) sulfite
Аннотация
Pourbaix diagrams of Cu–H2SO4–H2O and Ni–H2SO4–H2O systems have been refined, and stability regions of the sulfite phases have been determined. State diagrams of double copper(I)–copper(II) and copper(I)–nickel(II) sulfites have been constructed. Double copper(I)–nickel(II) sulfite has been isolated from aqueous solutions saturated with sulfur dioxide. The solutions at different ratios of the metals have been studied by spectrophotometry; the isolated double sulfite has been studied by X-ray diffraction, IR spectroscopy, dispersion analysis, and thermal analysis. Fundamentals of thermodynamic prognostication of the Cu2SO3·MSO3 double sulfites synthesis have been elaborated.
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Atom states and interatomic interactions in perovskite-like oxides: XXXV. Magnetic properties of solid solutions of lanthanum manganites doped with ytterbium and calcium in LaAlO3
Аннотация
The solid solutions La1–YYbyAlO3 (y = 0.01–0.20) and La1–0.397xYb0.067xCa0.33xMnxAl1–xO3 (x = 0.01–0.10) were studied by magnetic dilution method. The state of paramagnetic elements and the character of exchange interactions between them were determined on the basis of examination of magnetic properties. Clustering of manganese atoms in the La1–0.397xYb0.067xCa0.33xMnxAl1–xO3 solid solution, as distinct from the La1–0.67xCa0.33xMnxAl1–xO3 solid solutions studied before, is determined by the presence of ytterbium atoms in the perovskite structure of the complex oxides under study.
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Promoting non-transition metal alkylation with organic halides in the presence of binary systems based on an organometallic compound and a transition metal compound: VIII. Selectivity of the binary systems action
Аннотация
Selectivity of action of binary systems based on an organometallic compound and a transition metal compound in a direct synthesis of organometallic compounds via alkylation of metals with organic halides has been considered. Study of the side reactions in the course of zinc and cadmium powders alkylation (gaseous hydrocarbons evolution) taken as an example has demonstrated that the increase in activity of the binary system components is accompanied by decrease in its selectivity. The intensity of the side reactions is steeply increased above certain temperature determined by the nature of the reactants and components of the binary system. The surface of the alkylated metal containing adatoms and small clusters of the transition metal promotes the side processes.
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Promoting non-transition metal alkylation with organic halides in the presence of binary systems based on an organometallic compound and a transition metal compound: IX. Alkylation of aluminum and concluding remarks
Аннотация
Study of aluminum powder alkylation with ethyl bromide in the presence of ethylaluminum sesquibromide and copper(I) iodide has revealed that binary systems based on an organometallic compound and a transition metal compound are efficient promotors of direct synthesis of organoaluminum compounds as well. Major conclusions drawn in a series of studies on non-transition metals (Zn, Cd, and Al) alkylation with organic halides in the presence of the binary systems are summarized.
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(4-Arylsulfamoyl)phenylcarbamic acid esters: I. Synthesis and activity against herpes viruses
Аннотация
Aiming to modify the biological activity of sulfonamides, a number of alkyl (4-arylsulfamoyl)- phenylcarbamates were prepared in 50–70% yield. Biological screening showed that the target compounds possessed a high activity against herpes viruses as well as a traditional antibiotic one.
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Features of reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with binucleophiles
Аннотация
Regardless of pH and a solvent nature the reactions of (E)-1-(β-aroylvinyl)pyridinium bromides with hydrazine led to the formation of pyrazole derivatives. The salts reacted with thiourea via intermediate formation of 4-arylpyrimidine-2-thiol to give (Z)-2-[(β-aroylvinyl)sulfanyl]-4-arylpyrimidines. In the case of N,N'-diphenylthiourea the reaction provided 6-aryl-3-aroyl-1-phenylpyridinium bromides. Pyridine hydrobromide liberated in the reaction course has a major influence on the process chemoselectivity.
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2-Hetarylimidazoles quaternization
Аннотация
Quaternization of 2-hetarylimidazoles by the action of methyl iodide in anhydrous benzene was performed. The reaction involving 1-methyl-2-pyridyl-1H-imidazoles was studied in detail. Relative rate of 2-hetarylimidazoles quaternization changes in parallel with their basicity. The alkylation of aza group was found to be very sensitive to steric factors. The methylation of 1-methyl-2-(3-pyridyl)-1H- and 1-methyl-2-(4- pyridyl)-1H-imidazoles was accompanied with the formation of isomeric quaternary imidazole and pyridine salts.
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Synthesis and properties of 4-phosphorylated derivatives of 5-hydroxyalkylamino-1,3-oxazoles
Аннотация
Reactions of derivatives of diethyl 1-acylamino-2,2,2-trichloroethylphosphonates with different pharmacophore aminoalkanols afforded new 5-hydroxyalkylamino-1,3-oxazole derivatives. The latter are promising substrates for producing new 4-phosphorylated peptidomimetics containing alcohol residues.
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Synthesis of new 1,3-thiazole derivatives from 2(5)-hydroxyalkyl-1,3-thiazole-5(2)-carbaldehydes
Аннотация
Reactions of substituted 2-hydroxyalkyl-1,3-thiazole-5-carbaldehydes and 5-hydroxyalkyl-1,3-thiazole-2-carbaldehydes with phenylhydrazine, isoniazid, N-substituted rhodanines were performed as well as Biginelli reaction with acetoacetic ester and urea. As a result, new 1,3-thiazole derivatives were obtained. They are of interest as potential bioactive substances.
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Synthesis of 6-methyl-2-[2-phenyl-2-(arylhydrazono)ethyl]-3Н-pyrimidine-4-ones and their oxidation by hydrogen peroxide and selenium dioxide
Аннотация
The reaction of 6-methyl-2-(2-oxo-2-phenylethylidene)-2,3-dihydropyrimidine-4(1H)-one with arylhydrazines leads in high yields to the corresponding hydrazones, in which the ethylidene fragment of the starting compound is transformed to the ethylene fragment. By oxidation of the hydrazones with hydrogen peroxide or selenium dioxide the corresponding 6-methyl-2-[2-phenyl-2-(arylhydrazono)acetyl]-3H-pyrimidine-4-ones were synthesized.
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Multicomponent cyclothiomethylation of phenylenediamines and 4,4'-diaminodiphenyls with formaldehyde and 1,2-ethanedithiol
Аннотация
One-pot synthesis of bis-1,5,3-dithiazepanes by cyclothiomethylation of o-phenylenediamine, 4,4'-diaminodiphenyl, 4,4'-diaminodiphenyl oxide, and 4,4'-diaminodiphenylmethane with formaldehyde and 1,2- ethanedithiol was performed. Sorption properties of the newly synthesized bis[4-(1,5,3-dithiazepan-3-yl)-phenyl] oxide were investigated by the batch technique. High efficiency of the recovery of palladium(II) with this reagent from hydrochloric acid solutions at room temperature was shown.
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Synthesis and structure of amides of 4-aryl(hetaryl)-2-pyrrolidone-3-carboxylic acids
Аннотация
Amides of 4-aryl(hetaryl)-2-pyrrolidone-3-carboxylic acids have been prepared via ammonolysis of the corresponding esters of pyrrolidone carboxylic acids. The products structure has been characterized by means of IR, 1H NMR, 1H–13C HMQC, and HMBC spectroscopy.
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3-(Furyl)-3-(diethoxyphosphoryl)acrylates: Synthesis and reaction with nitromethane
Аннотация
A series of 3-(furyl)-3-(diethoxyphosphoryl)acrylates was synthesized by the reaction of 2- and 3-furoyl phosphonates with ethoxycarbonylmethylenetriphenylphosphorane. It was shown that in all cases diethoxyphosphoryl and ester groups were in trans-position with respect to the double bond disregarding the structure of the furan fragment. Potassium fluoride catalyzed addition of nitromethane to the compounds synthesized was studied. It was found that this reaction proceeded regioselectively to form 2-[(furyl)(diethoxyphosphoryl) methyl]-3-nitropropanoic acids.
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Reaction of trichlorides of phosphono carboxylic acids with acetylacetone, acetoacetic ester, and phenols
Аннотация
Reactions of trichloride of phosphono carboxylic acid with β-dicarbonyl compounds proceed at the active methylene group with the formation of the С-acylation product with a small admixture of the product of O-acylation. The C-acylation products undergo intramolecular condensation to form 1,2-oxophosphorines and compounds of the phosphate structure. The condensation of trichlorides with phenols proceeds selectively at the carbonyl carbon atom leading to C-phenyl esters. With more acidic phenols the splitting of the Р–С bond in the substitution product occurs.
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Selective and thermodynamic properties of supramolecular liquid-crystalline derivatives of azobenzene and biphenyl as stationary phases for gas chromatography
Аннотация
Smectic phase of formyl derivatives of azobenzene has been identified by means of polarization thermomicroscopy using a miscibility criterion. The study of dielectric properties and simulation of dipole moments and Kirkwood correlation factors have revealed that azobenzene and biphenyl derivatives containing hydroxy end group in the aliphatic terminal substituent can form supramolecules and linear associates stabilized by hydrogen bonds. The sorbents based on the studied liquid crystals have exhibited high structural selectivity with respect to isomers of various organic compounds. Thermodynamic manifestations of the specific mesogen–non-mesomorphic sorbate interactions have been revealed.
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Lability of spin state of Fe(III) complexes with tetradentate Schiff’s bases
Аннотация
[FeLX2]Y [L = N,N'-ethylenebis(salicylimine) (salen), N,N'-ethylenebis(acetylacetonylimine) (acen), or N,N'-ethylenebis(3-methyloxysalicylimine) (vanen); X = imidazole or N-methylimidazole; Y = BF4, ClO4, or BPh4] compounds have been prepared and studied by means of EPR and magnetic susceptibility measurements at 5–300 K. It has been shown that the different electron-donating properties of acen and salen planar ligands result in different spin states of Fe(III) ions. Intermolecular π-interactions of the outer-sphere BPh4 ion affect the complexes spin state as well.
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Synthesis and structure of silver complexes [Ph3(i-Pr)P]+2[Ag2I4]2− and [Ph3MeP]+n[Ag3I4]–n
Аннотация
Complexes [Ph3(i-Pr)P]+2[Ag2I4]2- and [Ph3MeP]+n[Ag3I4]–n were synthesized by the reaction of alkyl (triphenyl)phosphonium iodides with silver iodide in dimethyl sulfoxide. Triphenylalkylphosphonium cations have a tetrahedral configuration. Silver atoms in binuclear anions [Ag2I4]2- are characterized by trigonal coordination, the iodine coordination number being 2 or 1. In the polymeric anions [Ag3I4]–n the silver coordination number is 4 and that of iodine, 2, 3, or 4.
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Azomethine imines of pyrazolidone series and their bis-chelate Ni(II), Zn(II), Cd(II) complexes. Quantum chemical simulation
Аннотация
Prototropic processes in the molecules of azomethine imines with 2-pyrrolylmethylidene fragment were studied by the density functional theory (DFT) method and the most stable by energy isomers with the intramolecular hydrogen bond between the nitrogen atoms of the pyrrole and the pyrazole rings were found. The energy barriers of the reactions of intramolecular proton transfer were estimated. Based on quantum chemical calculations of the molecular structure of azomethine imine bis-chelates ML2 [M = Ni(II), Zn(II), Cd(II)] with the coordination unit MN2N2 the most stable configurations of the complexes were determined.
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Structure and magnetic properties of 2,4,6,8-tetra(tert-butyl)phenoxazin-1-one adducts with cobalt(II) salts
Аннотация
Complex formation reaction of redox-active 2,4,6,8-tetra(tert-butyl)phenoxazin-1-one with cobalt(II) chloride leading to the dimeric adduct has been studied. UV spectroscopy studies have revealed the equilibrium of the formed adduct with dissociated form of the complex in the acetonitrile solution. In the presence of ethylene glycol, the complex formation with cobalt(II) perchlorate has afforded the high-spin trimolecular adduct. Crystal structure of the obtained adducts has been studied by means of X-ray diffraction analysis.
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Spectral parameters of derivatives of methylpheophorbide a and chlorin e6, and their complex formation with Cu(II): The effects of structural fragments of the molecules and the solvent nature
Аннотация
Spectral (proton magnetic resonance and electronic absorption) parameters of the series of pyro-, meso-, and chlorin derivatives of methylpheophorbide a and kinetics of their complex formation with copper(II) nitrate in organic media have been studied.
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Phenylsulfanyl(fluoro)-substituted phthalocyanine nickel complexes: Synthesis and self-association
Аннотация
By cross-condensation of 4,5-bis(phenylsulfanyl)phthalonitrile (A) with tetrafluorophthalo-nitrile (B) in the presence of nickel acetate nickel phthalocyanines of the type A4, A3B, ABAB, AABB were synthesized. Their spectral properties were studied and the propensity to association in benzene solutions was revealed. The concentration of complexes where the association becomes notable decreases with the increased dipole moment of the phthalocyanine.
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Computer simulation of size effects and adsorption properties of one-wall carbon nanotubes (6,6)
Аннотация
Structure, electric and adsorption properties of carbon open-end nanotubes of (6,6) chirality consisting of 5–19 segments were studied by quantum-chemical methods AM1, PM3, LSDA/3-21G, B3LYP/6-31G. The size effects and adsorption properties of nanotubes are discussed.
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Complexation study of 4,13-didecyl-1,7,10,16-tetraoxa-4,13-diazacyclooctadecane (kryptofix 22DD) with the Co2+, Cr3+, Tl+, and UO22+ cations in acetonitrile, methanol, and their binary mixtures
Аннотация
Complexation between 4,13-didecyl-1,7,10,16-tetraoxa-4,13-diazacyclooctadecane (kryptofix 22DD) and the Co2+, Cr3+, Tl+, and UO22+ cations in acetonitrile, methanol, and their binary mixtures was studied by conductometry at different temperatures. The experimental results showed the formation of 1: 1 [ML] complexes between the studied metal cations and the macrocyclic ligand in most solvent systems. The stability constants of the resulting 1: 1 complexes were determined by computer fitting the conductance–mole ratio data. The stability of the metal–ion complexes in pure acetonitrile at 15 and 25°C was found to decrease in the order: [Tl (kryptofix 22DD)]+ > [Co(kryptofix 22DD)2+] > [UO2(kryptofix 22DD)]2+. Along with 1: 1 [ML] complexes, 2: 1 [M2L], 2: 2 [M2L2], 2: 3 [M2L3], 1: 2 [ML2], and 1: 3 [ML3] complexes are likely to be formed in some of the solvent systems. The thermodynamic parameters (ΔSc0, ΔHc0) of the complex formation in the studied nonaqueous solvents, obtained from the temperature dependences of the stability constants of the complexes, showed that the process is athermic.
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Magnetically-recoverable carbonaceous material: An efficient catalyst for the synthesis of 5-hydroxymethylfurfural and 5-ethoxymethylfurfural from carbohydrates
Аннотация
A novel, magnetically recoverable carbonaceous solid acid Fe3O4@C-SO3H catalyst for the conversion of carbohydrates to 5-ethoxymethylfurfural (EMF) was developed. The effect of the DMSO fraction in the ethanol-DMSO binary solvent on the distribution of the reaction products was investigated. The catalyst showed an excellent activity in the synthesis of EMF from fructose and 5-hydroxymethylfurfural (HMF). 5- Ethoxymethylfurfural was also obtained with a high yield of 64.2% in an ethanol–DMSO solvent system via one-step conversion of fructose. After reaction, the catalyst could be recovered by exposure of the reaction mixture to external magnetic field and reused several times without a loss of catalytic activity.
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Synthesis and antimicrobial evaluation of tricyclic macrocycles containing a chalcone moiety
Аннотация
A series of new tricyclic macrocycles containing a chalcone moiety were synthesized from chalcones through alkylation using different dibromoalkanes. All the synthesized compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectral data and evaluated for their in vitro antimicrobial activity.
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Synthesis, antimicrobial evaluation, and docking studies of some novel benzofuran based analogues of chalcone and 1,4-benzodiazepine
Аннотация
A series of novel {5-[4-hydroxy-3-(4-phenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-2-yl)benzyl]- benzofuran-2-yl}(phenyl)methanones (5a–5g) were prepared by the condensation of (E)-3-{5-[(2- benzoylbenzofuran-5-yl)methyl]-2-hydroxyphenyl}-1-phenylprop-2-en-1-one (chalcone) (4a) with various substituted o-phenylene diamines in the presence of oxalic acid as catalyst. The structures of all compounds were characterized by FTIR, 1H NMR, 13C NMR, and MS. The representative examples were screened in vitro for antimicrobial activity. Among all compounds 4g and 5g showed potent antibacterial activity, 4b and 5g showed good antifungal activity. The data was further compared with structure based investigations using docking studies with the crystal structure of adenosine-5'-(β,γ-imido)triphosphate (2ONJ) from Staphylococcus aureus for antibacterial activity and trypsin (1FY5) protein from Fusarium oxysporum for the antifungal activity. The score values estimated by genetic algorithm were found to have a good correlation with the experimental inhibitory potencies.
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Facile synthesis of novel (1-Aryl/alkyl-1H-1,2,3-triazol- 4-yl)methyl-2-bromo-4-methylthiazole-5-carboxylates by Cu(I) catalyzed click reaction
Аннотация
A number of novel thiazole-triazole heterocycles bearing (1-aryl/alkyl-1H-1,2,3-triazol-4-yl)methyl- 2-bromo-4-methylthiazole-5-carboxylates was synthesized through the click reaction. The structure of all new synthesized compounds was established by 1H and 13C NMR spectroscopy and mass spectrometry methods.
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Sc(OTf)3 catalyzed synthesis of novel 6-phenyl-6H-chromeno[4,3-b]quinolines and evaluation of their cytotoxicity
Аннотация
Novel 6-phenyl-6H-chromeno[4,3-b]quinoline derivatives have been prepared by reaction of 4-chloro-2-phenyl-2H-chromene-3-carbaldehyde with various aromatic amines using 5 mol % of Sc(OTf)3 in acetonitile. This is the first example of one-pot synthesis of 6-phenyl-6H-chromeno[4,3-b]quinoline from 4-chloro-2-phenyl-2H-chromene-3-carbaldehyde at ambient temperature. Preliminary evaluation of cytotoxic activity of these chromeno[4,3-b]quinoline derivatives has been carried out. Some products exhibited anti cancer activity against two carcinoma cell lines A549 and B-16.
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Ultrasound-assisted synthesis of pyrazolo[1,2-b]phthalazines and dihydrospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazines] using TBAF as an efficient phase-transfer catalyst
Аннотация
Tetrabutylammonim fluoride has been used as an efficient catalyst for synthesis of pyrazolo[1,2-b]-phthalazine-5,10-diones and dihydrospiro[indoline-3,1'-pyrazolo[1,2-b]phthalazines] by one-pot three-component reaction of phthalhydrazide, aromatic aldehydes or isatin derivatives, with malononitrile in water under ultrasond irradiation. This rapid method gave the products in high yield.
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Synthesis of novel 2-phenoxybenzo[g][1,2,4]triazolo[1,5-a]quinazoline and its derivatives starting with diphenyl-N-cyanoimidocarbonate
Аннотация
Cyclocondensation reaction of 3-hydrazinyl-2-naphthoic acid with diphenyl-N-cyanoimidocarbonate furnished the target 2-phenoxy-benzo[g][1,2,4]triazolo[1,5-a]quinazolin-5(4H)-one (1) in high yield. Alkylation, thionation and chlorination of the lactam group in the compound 1 produced a variety of derivatives 2–17. Their structures were characterized by NMR and HREI-MS analyses.
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Synthesis and characterization of green-emitting phosphorescent Ir(III) complexes based on phenyl benzimidazole ligand
Аннотация
Several new Ir(III) complexes with 2-(4-bromophenyl)-1H-benzo[d]imidazole or 2-(4-bromophenyl)- 1-methyl-benzo[d]imidazole ligands as cylcometalated ligand and acetylacetonate or picolinate as the ancillary ligand were synthesized and their structures and photophysical properties were characterized. HOMO and LUMO energy levels and the molecular structures of Ir(III) complexes were scrutinized by DFT calculations. The complexes exhibited green luminescence at the maximum emission peaks at ca 495–522 nm. The methyl group substituent and replacing of acetylacetonate with picolinate complex can enhance the complex thermal stability. HOMO energy levels of the complexes vary from –4.99 to –5.44 eV, the LUMO energy levels are between –1.52 and –1.97 eV.
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Microwave assisted synthesis of substituted (Z)-2-{[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol- 4-yl]methylene}benzofuran-3(2H)-ones and their antimicrobial activity
Аннотация
Aurones, pyrazole and thiophene scaffolds are known for their potential antimicrobial activity. Herein, we have synthesized hybrid compounds containing three substituted (Z)-2-{[1-phenyl-3-(thiophen-2-yl)- 1H-pyrazol-4-yl]methylene}benzofuran-3(2H)-ones that had been produced from substituted (E)-1-(2-hydroxyphenyl)- 3-[1-phenyl-3-(thiophen-2-yl)-1H-pyrazol-4-yl]prop-2-en-1-ones in high yields. All synthesized compounds were tested in vitro for their antimicrobial activity. Several of those demonstrated promising activity against some fungal and bacterial strains.
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Synthesis, single crystal x-ray analysis, and antimicrobial activity of new (22E)-N'-(4-methoxybenzylidene)-2-[3-cyano-7,8-dihydro-4-(5-methylfuran-2-yl)-2-oxo-2H-pyrano[4,3-b]pyridin-1(5H)-yl]acetohydrazide
Аннотация
(22E)-N'-(4-Methoxybenzylidene)-2-[3-cyano-7,8-dihydro-4-(5-methylfuran-2-yl)-2-oxo-2H-pyrano[ 4,3-b]pyridin-1(5H)-yl]acetohydrazide (2) was synthesized from 2-[3-cyano-7,8-dihydro-4-(5-methylfuran- 2-yl)-2-oxo-2H-pyrano[4,3-b]pyridin-1(5H)-yl]acetohydrazide (1) as starting material with 4-methoxybenzaldehyde. The product 22 was evaluated for antimicrobial activity against gram positive and gram negative bacteria in comparison with Vebromycine as the standard antibiotics. Compound 2, C24H22N4O5, crystallized as triclinic, P-1, a = 8.3496(5) Å, b = 10.9465(9) Å, c = 12.1495(9) Å, a = 74.694(4)°, β = 84.793(3)°, γ = 84.495 (3)°, V = 1063.64(13) Å3, Z = 2.
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Letters to the Editor
New method of synthesis of naphtylthioacetic acids 1-dialkylamides from 4-(1-naphthyl)-1,2,3-thiadiazole
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Synthesis, structure, and antioxidant activity of anabasinium O,O-dimethylthiophosphate
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3,5- and 3,6-disubstituted 3,4-dihydroquinazolines
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Formation of tetrakis[tri(2-chloroethyl)phosphate]diaquacobalt(II) tetrachlorocobaltate(II)
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Features of “secondary” silica interaction with ammonium molybdate in the porous space of high silica glass in acidic medium
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