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Vol 88, No 1 (2018)

Article

Solubility of d-Element Salts in Organic and Aqueous–Organic Solvents: VI.1 Structure and Thermal Stability of Cadmium Iodide and Bromide Solvates with Dimethylacetamide and Dimethylformamide

Bogachev N.A., Starova G.L., Razzhivin A.V., Skripkin M.Y., Nikolskii A.B.

Abstract

Five solvates, [CdBr2(DMF)]n, [CdBr2(DMA)]n, [CdI2(DMF)]n, [Cd(DMF)6][Cd2I6], and {[Cd(DMA)6][Cd5I12]n}m, were isolated from the ternary systems CdX2–L–H2O (X = Br, I; L = N,N-dimethylacetamide, N,N-dimethylformamide) and characterized by the X-ray single crystal analysis. The structures of the first three solvates is similar to each other in structures and represent a one-dimensional polymer chain, the fourth solvate has the discrete structure containing [Cd(DMF)6]2+ and [Cd2I6]2– ions, and the fifth solvate contains discrete [Cd(DMA)6]2+ cations and the polymer anionic fragment [Cd5I12]n2n.

Russian Journal of General Chemistry. 2018;88(1):1-6
pages 1-6 views

Chromato–Mass Spectrometric Identification of Unusual Products of 4-Isopropylphenol Oxidation in Aqueous Solutions

Zenkevich I.G., Pushkareva T.I.

Abstract

4-Isopropylphenol has been chosen as the simplest object to model the processes of oxidation of organic compounds with air oxygen in aqueous media, since it contains a hydrogen atom at the tertiary carbon atom in the α-position with benzene ring and a hydroxyl group enabling mass-spectrometric detection of the products in the negative ions mode. It has been stated that oxidation of 4-isopropylphenol with air oxygen in aqueous media becomes noticeable as the solution pH approaches the рKа value of the substrate (10.25). The major product [4-isopropyl-2-(4-isopropylphenoxy)phenol] is formed via nucleophilic addition of the starting 4-isopropylphenol at the intermediate product of its oxidation, quinone methide. Intensity of electrochemical oxidation can be tubed by changing the electrode potential. The highest conversion of 4-isopropylphenol has been observed at potential 1.5–3.0 V, the formed compounds being the products of transformation of the same quinone methide intermediate. The obtained data have explained the formation and diversity of dimeric and oligomeric products of oxidation of natural flavonoids.

Russian Journal of General Chemistry. 2018;88(1):7-14
pages 7-14 views

Methylation of Aliphatic and Aromatic Carboxylic Acids with Dimethyl Carbonate under the Influence of Manganese and Iron Carbonyls

Khusnutdinov R.I., Shchadneva N.A., Mayakova Y.Y.

Abstract

The synthesis of methyl esters has been carried out via the reaction of aliphatic and aromatic carboxylic acids with dimethyl carbonate in the presence of manganese and iron carbonyls. The optimal ratio of catalyst and reagents and other conditions for the synthesis of methyl esters of carboxylic acids with high yield have been found.

Russian Journal of General Chemistry. 2018;88(1):15-19
pages 15-19 views

Colloid and Nanosized Catalysts in Organic Synthesis: XIX.1 Influence of the Support Nature on Hydrogenation Catalysis of Cyclic Olefins by Nickel Nanoparticles

Popov Y.V., Mokhov V.M., Nebykov D.N., Shcherbakova K.V., Dontsova A.A.

Abstract

Gas-phase hydrogenation of cycloalkenes in the presence of nickel nanoparticles supported on Ceokar-2, BAU-A activated carbon, alumina, and NaX zeolite proceeds at 140–240°C and atmospheric pressure of hydrogen. The conversion and selectivity depend on the type of support and on the hydrogen excess.

Russian Journal of General Chemistry. 2018;88(1):20-24
pages 20-24 views

Hydrosilylation of Allyl Ethers in the Presence of Supported Sulfur-Containing Platinum(II) Complexes

de Vekki D.A., Il’ina M.A., Skvortsov N.K.

Abstract

Hydrosilylation of allyl ethyl, allyl butyl, allyl glycidyl, allyl benzyl, and allyl phenyl ethers by 1,1,3,3-tetramethyldisiloxane in the presence of supported sulfur-containing platinum(II) complexes with the general formula [{SiO2}O2Si(Me)(CH2)3SR]2PtCl2 (R = Bu, Hex, Bn; {SiO2} is silica surface) and side processes have been studied.

Russian Journal of General Chemistry. 2018;88(1):25-35
pages 25-35 views

Synthesis and Structure of Geminally Activated 1-Nitro-4-phenylbuta-1,3-dienes

Baichurin R.I., Alizada L.M., Aboskalova N.I., Makarenko S.V.

Abstract

The condensation of cinnamaldehyde with nitro-substituted CH acids (ethyl nitroacetate, nitroacetone, nitroacetophenone, and nitroacetonitrile) afforded a series of geminally activated 1-nitro-4-phenylbuta- 1,3-dienes. Their structure was determined on the basis of a set of 1H, 13C–{1H}, 15N NMR, and IR spectra.

Russian Journal of General Chemistry. 2018;88(1):36-40
pages 36-40 views

Azomethines Based on Pyridoxal-Derived Aromatic Aldehydes

Kibardina L.K., Trifonov A.V., Ivanova Y.I., Pudovik M.A., Pudovik E.M., Burilov A.R.

Abstract

The reaction of pyridoxal with 2,4-dihydroxybenzaldehyde in a hydrochloric acid solution gave 1-(5-formyl-2,4-dihydroxyphenyl)-7-hydroxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-5-ium chloride. Treatment of the latter with sodium hydride in ethanol afforded a free aldehyde in 85% yield. A series of azomethines and imidazolidines was obtained by reacting the obtained aldehyde with various amines and diamines.

Russian Journal of General Chemistry. 2018;88(1):41-47
pages 41-47 views

A Study on Hydrolytic Stability of Isatin N-Mannich Bases

Orlova D.D., Novikova D.S., Garabadzhiu A.V., Tribulovich V.G.

Abstract

Stability parameters of biologically active compounds with N-Mannich base motif in their structure, which is susceptible to hydrolysis, have been studied. A procedure for the synthesis of small molecule compounds reactivating the function of the p53 tumor suppressor protein was developed, and the dependence of the Mannich base degradation rate on the structure of the compounds was established. For the hydrolysis reaction we determined the rate constants and calculated ρ, ΔG#, ΔH, and ΔS. Modifications of active compounds that retain the activity at the maximum possible stability were proposed.

Russian Journal of General Chemistry. 2018;88(1):48-56
pages 48-56 views

Isatin Derivatives Containing Sterically Hindered Phenolic Fragment and Water-Soluble Acyl Hydrazones on Their Basis: Synthesis and Antimicrobial Activity

Bogdanov A.V., Zaripova I.F., Voloshina A.D., Strobykina A.S., Kulik N.V., Bukharov S.V., Mironov V.F.

Abstract

Condensation reactions of isatin derivatives with 3,5-di(tert-butyl)-4-hydroxybenzyl acetate and the Girard’s reagent T has afforded a series of novel water-soluble isatin-3-acyl hydrazones containing a sterically hindered phenolic fragment in position 1 of the heterocycle; antimicrobial activity of the products has been estimated. It has been shown that the isatin derivatives with bromine or methoxy substituent in the benzo fragment as well as the acyl hydrazones containing 5-methyl or 5-ethyl group are the most active against Staphylococcus aureus and Bacillus cereus.

Russian Journal of General Chemistry. 2018;88(1):57-67
pages 57-67 views

Synthesis and Antioxidant Activity of Sterically Hindered Phenol Derivatives of Carboxy- and Sulfobetaines

Tagasheva R.G., Shakirova E.R., Bukharov S.V., Galkina I.V., Ziyatdinova G.K., Musin R.Z., Rizvanov I.K.

Abstract

New multifunctional antioxidants based on carboxy- and sulfobetaines with sterically hindered phenol fragments were synthesized. The antioxidant capacity of the compounds determined in the reactions of their oxidation by electrogenerated bromine is comparable to that of ascorbic acid and ionol.

Russian Journal of General Chemistry. 2018;88(1):68-72
pages 68-72 views

Unexpected Reaction of Ethyl 4-(Chloromethyl)pyrazolo- [5,1-c][1,2,4]triazine-3-carboxylates with Thiourea and Its Mechanism

Ledenyova I.V., Falaleev A.V., Shikhaliev K.S., Ryzhkova E.A., Zubkov F.I.

Abstract

The reaction of ethyl 4-(chloromethyl)pyrazolo[5,1-c][1,2,4]triazine-3-carboxylates with thiourea in dimethylformamide involves ANRORC rearrangement (Addition of the Nucleophile, Ring Opening, and Ring Closure) followed by N-formylation to give N-{5-(4-oxo-8-phenyl-1,4-dihydropyrazolo[5,1-c][1,2,4]-triazin-3-yl)-1,3-triazol-2-yl}formamides whose structure was confirmed by X-ray analysis. The reaction mechanism has been studied by HPLC/MS.

Russian Journal of General Chemistry. 2018;88(1):73-79
pages 73-79 views

Reactivity of α-Amino Acids in the Reaction with Esters in Aqueous–1,4-Dioxane Media

Kochetova L.B., Kustova T.P., Kuritsyn L.V.

Abstract

The kinetics of the reaction of a series of α-amino acids with 4-nitrophenyl acetate, 4-nitrophenyl benzoate, and 2,4,6-trinitrophenyl benzoate in aqueous 1,4-dioxane medium has been studied. Kinetics of the reactions involving 4-nitrophenyl acetate and 2,4,6-trinitrophenyl benzoate has complied with the Brønsted dependence and revealed linear correlation between rate constant logarithm and the energy difference of the frontier orbitals of α-amino acids anions.

Russian Journal of General Chemistry. 2018;88(1):80-85
pages 80-85 views

Macroheterocyclic Compounds with Thiadiazole Fragments. Synthesis and Properties

Berezina G.R.

Abstract

The reactions of 1-imino-2-phenyl-1H-inden-3-amine with 3,5-diamino-1,2,4- and 2,5-diamino-1,3,4- thiadiazoles were used to synthesize linear 1: 2 and 2: 1 condensation products, as well as symmetrical macroheterocyclic compounds. The synthesized compounds were characterized by IR, UV, and 1Н NMR spectroscopy.

Russian Journal of General Chemistry. 2018;88(1):86-89
pages 86-89 views

Reactions of Unsaturated Ketones with Bis(trimethylsilyl) Hypophosphite

Tatarinov D.A., Kundina M.V., Dobrynin A.B., Mironov V.F.

Abstract

Bis(trimethylsilyl) hypophosphite reacts with unsaturated ketones (methyl vinyl ketone and mesityl oxide) to give, depending on the reaction conditions, 1: 1 or 1: 2 adducts after hydrolysis. It was found that the intramolecular cyclization of the 1: 2 reaction product with mesityl oxide, trimethylsilyl bis(2-methyl-4- oxopentan-2-yl)phosphinate, yields, after hydrolysis, a phosphorinane with exocyclic carbonyl and hydroxyl groups.

Russian Journal of General Chemistry. 2018;88(1):90-95
pages 90-95 views

Mechanism of Protodephenylation of 1,3-Silaheterocyclohexanes. Effect of Heteroatom

Kirpichenko S.V., Albanov A.I., Shainyan B.A.

Abstract

The mechanism of electrophilic cleavage of the Si–Ph bond in 1,3-silaheterocyclohexanes is investigated. 3-Aryl-3-silatetrahydropyrans are shown to be less prone to the cleavage of the Si–Ph bond under the action of trifluromethanesulfonic acid than the corresponding 3-silathianes or silacyclohexanes. The effect of heteroatom (N, O, S) in the ring on the functionalization at the silicon atom in 1,3-silaheterocyclohexanes was studied experimentally by the method of NMR spectroscopy and theoretically by DFT calculations and the mechanism was suggested of dephenylation as a function of the nature of heteroatom.

Russian Journal of General Chemistry. 2018;88(1):96-102
pages 96-102 views

Condensation Products of D-Ribose with Thiol-Containing Hydrazides and Gold Glyconanoparticles Thereof

Ershov A.Y., Vasil’eva M.Y., Lagoda I.V., Baigil’din V.A., Nasledov D.G., Kuleshova L.Y., Yakimanskii A.V.

Abstract

The accessible D-ribose mercaptoacetyl-, 3-mercaptopropionyl-, and 2-mercaprobenzoylhydrazones were used to develop a method of synthesis of gold glyconanoparticles with the average particle diameter of 10–40 nm and a low polydispersity index.

Russian Journal of General Chemistry. 2018;88(1):103-108
pages 103-108 views

Synthesis of Silver Glyconanoparticles Based on 3-Thiopropionylhydrazones of Mono- and Disaccharides

Vasileva M.Y., Ershov A.Y., Baigildin V.A., Lagoda I.V., Kuleshova L.Y., Shtro A.A., Zarubaev V.V., Yakimanskii A.V.

Abstract

A method of synthesis of silver glyconanoparticles with average particle size 15–40 nm and low polydispersity index based on available 3-thiopropionylhydrazones of mono- and disaccharides has been elaborated. The prepared compounds have exhibited high antifungal, antibacterial, and antiviral activity and are promising for further comprehensive study.

Russian Journal of General Chemistry. 2018;88(1):109-113
pages 109-113 views

Influence of Synthesis Conditions on the Morphology and Spectral-Luminescent Properties of Films of Organic-Inorganic Perovskite CH3NH3PbI2.98Cl0.02

Belous A.G., V’yunov O.I., Kobylianska S.D., Ishchenko A.A., Kulinich A.V.

Abstract

The influence of the synthesis conditions (rotation speed used for spin-coating deposition of the film, film drying temperature, and the ratio of the PbI2 and CH3NH3I reactants in solutions) on the microstructure, phase composition, and spectral-luminescent properties of films of organic-inorganic perovskite CH3NH3PbI3–xClx (x = 0, 0.02) was elucidated.

Russian Journal of General Chemistry. 2018;88(1):114-119
pages 114-119 views

Membrane Extraction of Lithium and Sodium Ions with 2-Ethylhexyl Hydrogen [Bis(2-ethylhexyl)amino]methylphosphonate

Garipova A.R., Kamkina A.G., Urazgalieva A.A., Garifzyanov A.R., Cherkasov R.A.

Abstract

Lithium and sodium ion transport through membranes impregnated with a solution of 2-ethylhexyl hydrogen [bis(2-ethylhexyl)amino]methylphosphonate in kerosene has been studied. Factors determining the efficiency and selectivity of membrane extraction have been determined. Introduction of neutral aminomethylphosphine oxide into the membrane phase has been shown to enhance the selectivity for lithium ions.

Russian Journal of General Chemistry. 2018;88(1):120-123
pages 120-123 views

Letters to the Editor

Features of Reactions of Some 1-Arylaminomethylisatins with Girard’s Reagent T

Bogdanov A.V., Gil’fanova A.R., Zaripova I.F., Mironov V.F.

Abstract

Depending on the structure of the substituent at the endocyclic nitrogen atom, the reactions of aminomethylisatins with the Girard’s reagent T can proceed both with the elimination of the aminomethyl group and with its retention resulting in the formation of the corresponding positively charged isatin-3-acylhydrazones.

Russian Journal of General Chemistry. 2018;88(1):124-126
pages 124-126 views

Synthesis of 2,3-Dihydro[1,4]oxazino[2,3,4-ij]quinolinium Bromide and Its Reaction with Sodium Hydroxide

Kim D.G., Vasilenko A.V., Melent’ev A.B.

Abstract

The reaction of quinolin-8-ol with 1,2-dibromoethane in dimethylformamide gave 2,3-dihydro[1,4]-oxazino[2,3,4-ij]quinolinium bromide which reacted with aqueous sodium hydroxide to afford 2,3,4,5-tetrahydro[1,4]oxazino[2,3,4-ij]quinoline, 2,3,4,5-tetrahydro[1,4]oxazino[2,3,4-ij]quinolin-5-ol, and 2,3,4,5-tetrahydro[1,4]oxazino[2,3,4-ij]quinolin-5-one.

Russian Journal of General Chemistry. 2018;88(1):127-130
pages 127-130 views

Reaction of 4-Chloro-6-[1-(vinylsulfonyl)pyrrolidin-2-yl]benzene-1,3-diol with Some Amines

Smolobochkin A.V., Anikina E.A., Gazizov A.S., Vagapova L.I., Burilov A.R., Pudovik M.A.

Abstract

4-Chloro-6-[1-(vinylsulfonyl)pyrrolidin-2-yl]benzene-1,3-diol prepared by the reaction of 2-ethoxypyrrolidine with 4-chlororesorcinol was introduced into the aza-Michael reaction with various amines which led to the formation of new 1-sulfonyl-2-arylpyrrolidines

Russian Journal of General Chemistry. 2018;88(1):131-135
pages 131-135 views

Synthesis of Methyl-Substituted Derivatives of 5-Hydroxy-6-methyluracil

Petrova S.F., Nugumanov T.R., Lobov A.N., Spirikhin L.V., Murinov Y.I., Ivanov S.P.

Abstract

5-Hydroxy-3,6-dimethyluracil, 5-methoxy-1,3,6-trimethyluracil, earlier unknown 5-methoxy-6- methyluracil, 5-methoxy-1,6-dimethyluracil, and 5-methoxy-3,6-dimethyluracil have been synthesized via alkylation of 5-hydroxy-6-methyluracil with dimethylsulfate in aqueous-alkaline media. The obtained compounds have been identified using 1Н, 13С, and 15N NMR spectroscopy.

Russian Journal of General Chemistry. 2018;88(1):136-139
pages 136-139 views

New Bicyclic Phosphonates with Benzyl Fragments

Sadykova Y.M., Voronina Y.K., Burilov A.R., Pudovik M.A.

Abstract

New bicyclic mono- and dibenzyl-substituted phosphonates based on resorcinol and methyl resorcinol were synthesized. Structure of the disubstituted bicyclic phosphonate was established by X-ray diffraction method.

Russian Journal of General Chemistry. 2018;88(1):140-142
pages 140-142 views

Phosphorylation of Oxyethylated Calix[4]resorcinols with Phosphorous Acid Amides

Gibadullina E.M., Kayupov A.R., Pudovik M.A., Burilov A.R.

Abstract

The reaction of octa-2-hydroxyethylated calix[4]resorcinols with phosphorous acid amides and the subsequent thionylation by elemental sulfur afforded hydrolytically stable oxyethyl calix[4]resorcinols containing eight thiophosphoryl fragments.

Russian Journal of General Chemistry. 2018;88(1):143-146
pages 143-146 views

Synthesis and Some Reactions of New Acetals Containing Aminoethylenephosphoryl Fragment

Vagapova L.I., Sadykova Y.M., Makhrus E.M., Burilov A.R., Eltaev A.S., Kudiyar T.A., Pudovik M.A.

Abstract

Phosphonoethylated amino acetals were synthesized for the first time by reacting vinylphosphonates with α- and γ-aminoacetals. The reaction of 2-methylresorcinol with the acetals in ethanol in the presence of hydrochloric acid afforded the first representative of diarylbutylamines containing β-aminoethylenephosphoryl fragment.

Russian Journal of General Chemistry. 2018;88(1):147-150
pages 147-150 views

Synthesis of 2-Naphthylacetylene Selenides from 4-(2-Naphthyl)-1,2,3-selenadiazole

Yekhlef M., Petrov M.L., Pevzner L.M., Ponyaev A.I.

Abstract

4-(2-Naphthyl)-1,2,3-selenadiazole under the action of bases eagerly decomposes with liberation of nitrogen to form potassium 2-(2-naphthyl)ethyneselenolate. By further treatment of the reaction mixture with the excess of alkyl halide the corresponding methyl- and butyl-2-(2-naphthyl)-1-ethynyl selenides were obtained. In the absence of alkyl halides treating with the potassium hydroxide ethanol solution yields 4-(2- naphthyl)-2-[1-(2-naphthyl)-2-[1-(2-naphthyl)methylidenee]-1,3-diselenol.

Russian Journal of General Chemistry. 2018;88(1):151-153
pages 151-153 views

Synthesis and Structure of a Copper(II) Complex of N,N'-Bis(di-para-tolylphosphinoylmethyl)-1,8-diamino- 3,6-dioxaoctane

Garifzyanov A.R., Davletshina N.V., Gaynullin A.Z., Ivshin K.A., Kataeva O.N., Cherkasov R.A.

Abstract

A copper(II) complex of N,N'-bis(di-para-tolylphosphinoylmethyl)-1,8-diamino-3,6-dioxaoctane was synthesized and its crystal structure was established. The inner coordination sphere of the complex is a strongly distorted trigonal bipyramid. Coordination involves the phosphoryl oxygen atoms, nitrogen atoms, and ether oxygen atom, and one axial position is occupied by a water molecule.

Russian Journal of General Chemistry. 2018;88(1):154-157
pages 154-157 views

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