Stability and Reproducibility  of the Dimeric Motif in the Crystals  of Thioethers of 3-Bromo-5-Hydroxy-1- (4-Methylbenzyl)-1,5-Dihydro-2h-Pyrrol-2-Ones

Gerasimova, D. P.; Faizova, R. G.; Zakharychev, Dmitry V.; Saifina, Alina F.; Kurbangalieva, Almira; Лодочникова, О. А.

doi:10.1134/s0022476622100080

Cited by 2 publications

(1 citation statement)

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“…Unfavorable orientation of the H-atom with respect to carbonyl lone pairs in heterochiral crystals and a favorable one in homochiral crystals found not only for the studied compound but is reproduced for the entire series of currently known chiral thioethers of N-substituted 5-hydroxy-3-pyrrolin-2-ones. In particular, we have recently described three new heterochiral crystals belonging to the aforementioned series, and, as expected, all of them demonstrate an unfavorable (in terms of mutual arrangement of the donor and acceptor fragments) orientation of hydrogen bonds.…”

Section: Discussionsupporting

confidence: 75%

Homochiral versus Heterochiral Crystallization of 3-Pyrrolin-2-one Thioether Results in the Score 2:1 in Favor of Homochirality

Gerasimova

Zakharychev

Saifina

et al. 2022

Crystal Growth & Design

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A rare phase behavior of rac- 1-benzyl-3-bromo-4-[(4chlorophenyl)sulfanyl]-5-hydroxy-1,5-dihydro-2H-pyrrol-2-one, which consists of the formation of two normal monoclinic and hexagonal conglomerates and a monoclinic racemic compound, has been discovered by thermochemical and X-ray diffraction methods. Its monoclinic racemic compound is reproducibly formed as a result of the suspension by stirring the solid phase in hydrocarbons at room temperature, while routine crystallization from a solution leads to the formation of a mixture of the two conglomerates. Thermochemical data suggest that the monoclinic conglomerate is metastable within the entire temperature range, the monoclinic racemic crystal is stable under normal conditions (20 °C) up to 110 °C, and the hexagonal conglomerate is stable at elevated temperatures above 110 °C. The essential structural difference between the homo-and heterochiral crystals lies in the optimal mutual orientation of the donor and acceptor groups of the H-bonds for the former case and the unfavorable mutual orientation for the latter one.

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Section: Discussionsupporting

confidence: 75%