D. P. Gerasimova's research while affiliated with A.E. Arbuzov Institute of Organic and Physical Chemistry and other places
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Publications (21)
The interaction of propane-1,3-dithiol with the chiral bis-thioether, which combines two 2(5H)-furanone moieties, bridged through their carbon atoms C(4) by the propane-1,3-dithiol fragment, in DMF in the presence of potassium hydroxide or cesium carbonate resulted in the formation of an optically active fused bicyclic sulfur heterocycle, possessin...
Novel disulfinyl derivatives based on 3,4-dichloro-2(5H)-furanone, aliphatic dithiols, and monoterpene alcohols were synthesized. Chiral bis-thioethers in the molecules of which the dithiol fragment links two five-membered cycles at C4 atoms were obtained in the reactions of 5(S)-(l-menthyloxy)- and 5(S)-(l-bornyloxy)-2(5H)-furanones with ethane-1,...
A theoretical study of the association of phenyl and ortho-substituted aryl derivatives of lactic acid was carried out. Two variants of hydrogen-bonded associates in the gas phase were calculated: non-classical, actually found in the crystals, and simulated classical dimers. The energy advantage of classical dimers and the non-equivalence of diaste...
We synthesized the novel compound ethyl 12-sulfamoyl-abieta-8,11,13-trien-18-oate in good yield from ethyl 12-sulfo-abieta-8,11,13-trien-18-oate via a two-step protocol. The product was comprehensively characterized by one- and two-dimensional NMR methods, single-crystal X-ray diffraction, IR spectroscopy, and high-resolution mass spectrometry.
An unusual type of rac-7-chlorine-2,3,4a,6-tetrahydrofuro[2,3-b][1,4]oxathiin-6-one crystallization is reported. This compound crystallizes in the form of lamellar conglomerates where each single crystal is not optically pure but is only enantiomerically enriched by one optical antipode and displays optical rotation.
The crystal structures of four representatives of sulfinamides of the thiazine series are comparatively analyzed for the occurrence of different supramolecular associates, inter- and intramolecular interactions. With a similar molecular geometry, different packing motifs occur in the crystals yielding different-type supramolecular associates due to...
Two crystalline diastereomorphs of rac-1-benzyl-3-bromo-5-hydroxy-4-[(4-methylphenyl)sulfanyl]-1,5-dihydro-2Н-pyrrole-2-one are obtained and characterized: the racemic compound (P21/c) and the normal conglomerate (P65, P61). The conglomerate is shown to be more thermodynamically preferred while the racemic compound is a metastable form in the entir...
Two packing polymorphs of 5-hydroxy-1-(4-methylbenzyl)-3-chloro-4-[(4-chlorophenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one are studied by single-crystal and powder X-ray diffraction, IR spectroscopy, and differential scanning calorimetry. Classical hydrogen bonds and CL…O interactions have the fundamental importance for the formation of the supramole...
The work juxtaposes crystal structures of two hydrochlorides of eight-membered 1,5-diazaheterocycles with chiral aminoindanole fragments located at the nitrogen atoms and having similar configurations. In spite of chemical and stereochemical identity of a half of diazaheterocycle molecules, in crystals these compound are realized in the general pos...
Citations
... 1,3,13,14 They are also interested in other rare ways of crystallising chiral matter. [15][16][17][18][19][20][21][22][23][24][25][26][27][28] However, it is possible that the reasons for chiral discrimination lie precisely in trivial heterochiral crystallisation, which is much more common than homochiral crystallisation, and understanding these reasons may lead to insights into the relationship sought. In particular, it is possible to systematically change the structure of a chemical compound, analysing how this affects the manner it crystallises. ...
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... Далее в контексте развиваемого нашей группой стереохимического подхода к анализу кристаллической структуры [8][9][10][11] мы выполнили блок расчетов по топологическому анализу вычисленной электронной плотности () r и ее лапласиана 2 () r как для изолированной молекулы, так и для обоих вариантов димера. Мы исходили из предположения, что альтернативное участие либо одной, либо другой неподеленной электронной пары (НЭП) карбонильного атома кислорода напрямую соотносится с формированием первого или второго синтона. ...
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... We earlier revealed and reported formation of a completely asymmetric supramolecular associate as a specific cause of crystallization of a chiral organic compound with Z′ > 1 [11][12][13][14]. Such situation is possible when supramolecular chiral centers are formed at the stage of the associate formation (in addition to stable asymmetric centers of the molecule), and the resulting associate is composed of the molecules of supramolecular diastereomers. ...
... Sulfur-containing binucleophilic reagents have received less attention in contrast to the application of thiols in the reactions with 2(5H)-furanones, carried out under basic or acidic conditions. Thus, the interaction of furanone derivatives with S,O-, S,N-, and S,S-binucleophiles, such as 2-mercaptoethanol [14,15], o-aminothiophenol [16], thioamino acids and their derivatives [17], disodium 2-oxo-1,3-dithiole-4,5-dithiolate [18], ethane-1,2-dithiol [19], propane-1,3-dithiol [20], and 2,2 -oxydiethanethiol [21], are described. The use of these binucleophilic reagents in the reactions with 3,4-dichloroderivatives of 2(5H)-furanone allowed us to observe the structural diversity of the thiylation products on the basis of the unsaturated lactone ring, including thioethers, various bis-thioethers, sulfur-containing fused systems, and spiro bicyclic systems. ...
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... The methodology described was originally suggested by us 26 and has since been employed in other prior studies. 14,35,[49][50][51] Here, we will provide a detailed and improved step-by-step description of the calculations essential for constructing an energy diagram. ...
... The methodology described was originally suggested by us 26 and has since been employed in other prior studies. 14,35,[49][50][51] Here, we will provide a detailed and improved step-by-step description of the calculations essential for constructing an energy diagram. ...
