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CHIRALITY-DEPENDENT HYDROGEN BONDING AND ENERGY OF 1-BENZYL-3-BROMO-5-HYDROXY- 4-[(4-METHYLPHENYL)SULFANYL]-1,5-DIHYDRO- 2Н-PYRROLE-2-ONE DIASTEREOMORPHS

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Abstract

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 entire temperature range studied. These two modifications are formed as a mixture during routine crystallization from a solution and characterized by a similar density, however, their structures significantly differ in the parameters of hydrogen bonds. A small difference in the free energies of two phases at room temperature, which is found by differential scanning calorimetry, explains the experimental availability of both forms during crystallization from the solution. The formation of a stronger hydrogen bond in the conglomerate crystals, which is detected by X-ray diffraction and solid-state vibrational spectroscopy, may be explained by a more favorable arrangement of donor and acceptor groups of the neighboring molecules in a homochiral helix of the conglomerate as compared with a heterochiral dimer, which is the main motif in crystals of the racemic compound.

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Funding

The work was supported by Russian Science Foundation grant No. 17-13-01209.

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Authors and Affiliations

  1. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan, Russia

    D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, R. R. Fayzullin & O. A. Lodochnikova

  2. Butlerov Institute of Chemistry, Kazan (Volga Region) Federal University, Kazan, Russia

    D. P. Gerasimova, A. R. Zaripova, A. R. Kurbangalieva & O. A. Lodochnikova

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  1. D. P. Gerasimova
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  2. A. F. Saifina
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  3. D. V. Zakharychev
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  4. A. R. Zaripova
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  5. R. R. Fayzullin
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  6. A. R. Kurbangalieva
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  7. O. A. Lodochnikova
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Correspondence to D. P. Gerasimova.

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Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 5, pp. 781-794.https://doi.org/10.26902/JSC_id72892

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Gerasimova, D.P., Saifina, A.F., Zakharychev, D.V. et al. CHIRALITY-DEPENDENT HYDROGEN BONDING AND ENERGY OF 1-BENZYL-3-BROMO-5-HYDROXY- 4-[(4-METHYLPHENYL)SULFANYL]-1,5-DIHYDRO- 2Н-PYRROLE-2-ONE DIASTEREOMORPHS. J Struct Chem 62, 727–739 (2021). https://doi.org/10.1134/S0022476621050097

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  • DOI: https://doi.org/10.1134/S0022476621050097

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