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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

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Abstract

We confirm our previously formulated rule about the possibility of a spontaneous resolution of enantiomers of a series of 5-hydroxy-3-pyrrolin-2-one thioderivatives. Crystal packings of three racemic compounds are compared. A supramolecular associate of the same type (a hydrogen-bonded dimer) is found, which is differently packed in the 3D structure of the crystals.

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REFERENCES

  1. P. A. Levkin, V. Y. Torbeev, D. A. Lenev, and R. G. Kostyanovski. Top. Stereochem., 2006, 25, 81. https://doi.org/10.1002/0471785156.ch4

    Chapter  Google Scholar 

  2. J. Jacques, A. Collet, and S. H. Wilen. Enantiomers, Racemates and Resolutions. Krieger Publishing Company, 1994.

  3. L. Perez-Garcia and D. B. Amabilino. Chem. Soc. Rev., 2007, 36, 941. https://doi.org/10.1039/B610714A

    Article  CAS  PubMed  Google Scholar 

  4. D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, A. R. Zaripova, R. R. Fayzullin, A. R. Kurbangalieva, and O. A. Lodochnikova. J. Struct. Chem., 2021, 62(5), 727. https://doi.org/10.1134/S0022476621050097

    Article  CAS  Google Scholar 

  5. O. A. Lodochnikova, A. R. Zaripova, R. R. Fayzullin, A. I. Samigullina, I. I. Vandyukova, L. N. Potapova, and A. R. Kurbangalieva. CrystEngComm, 2018, 20, 3218. https://doi.org/10.1039/C8CE00369F

    Article  CAS  Google Scholar 

  6. D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, R. R. Fayzullin, A. R. Kurbangalieva, and O. A. Lodochnikova. CrystEngComm, 2021, 23, 3907. https://doi.org/10.1039/D1CE00227A

    Article  CAS  Google Scholar 

  7. D. P. Gerasimova, O. A. Lodochnikova, A. R. Kurbangalieva, and I. A. Litvinov. J. Struct. Chem., 2021, 62(9), 1425. https://doi.org/10.1134/S0022476621090110

    Article  CAS  Google Scholar 

  8. O. A. Lodochnikova, Y. K. Voronina, L. Z. Latypova, D. B. Krivolapov, A. R. Kurbangalieva, and I. A. Litvinov. Russ. Chem. Bull., 2013, 62, 1218. https://doi.org/10.1007/s11172-013-0167-1

    Article  CAS  Google Scholar 

  9. D. P. Gerasimova, R. R. Fayzullin, D. V. Zakharychev, A. F. Saifina, I. I. Vandyukova, A. R. Kurbangalieva, and O. A. Lodochnikova. Abstracts of Reports: X National Crystal Chemical Conference. Elbrus region, Russia, July 5-9, 2021. Chernogolovka, Russia: IPCP RAS, 2021, 80. [In Russian]

  10. O. A. Lodochnikova, L. S. Kosolapova, A. F. Saifina, A. T. Gubaidullin, R. R. Fayzullin, A. R. Khamatgalimov, I. A. Litvinov, and A. R. Kurbangalieva. CrystEngComm, 2017, 19, 7277. https://doi.org/10.1039/C7CE01717K

    Article  CAS  Google Scholar 

  11. D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, I. I. Vandyukova, R. R. Fayzullin, A. R. Kurbangalieva, and O. A. Lodochnikova. J. Struct. Chem., 2020, 61(3), 476. https://doi.org/10.1134/S0022476620030142

    Article  CAS  Google Scholar 

  12. L. Krause, R. Herbst-Irmer, G. M. Sheldrick, and D. Stalke. J. Appl. Crystallogr., 2015, 48, 3. https://doi.org/10.1107/S1600576714022985

    Article  CAS  Google Scholar 

  13. G. M. Sheldrick. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3. https://doi.org/10.1107/S2053273314026370

    Article  Google Scholar 

  14. G. M. Sheldrick. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3. https://doi.org/10.1107/S2053229614024218

    Article  Google Scholar 

  15. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. J. Puschmann. J. Appl. Crystallogr., 2009, 42, 339. https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  16. L. J. Farrugia. J. Appl. Crystallogr., 2012, 45, 849. https://doi.org/10.1107/S0021889812029111

    Article  CAS  Google Scholar 

  17. A. J. Gordon and R. A. Ford. The Chemists Companion: a Handbook of Practical Data, Techniques, and References. Wiley, 1972.

  18. H. Simonis. Chem. Ber., 1901, 34, 509. https://doi.org/10.1002/cber.19010340184

    Article  CAS  Google Scholar 

  19. L. Cao, S.-H. Luo, H.-Q. Wu, L.-Q. Chen, K. Jiang, Z.-F. Hao, and Z.-Y. Wang. Adv. Synth. Catal., 2017, 359, 2961. https://doi.org/10.1002/adsc.201700600

    Article  CAS  Google Scholar 

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Funding

Physicochemical studies were carried out in the Multi-Access Spectral Analytical Center of the Kazan Scientific Center, Russian Academy of Sciences and supported by the State Assignment of the Kazan Scientific Center, Russian Academy of Sciences.

The synthesis of the key compounds was supported by the Kazan Federal University Strategic Academic Leadership Program (Priority-2030).

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Correspondence to D. P. Gerasimova.

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Russian Text © The Author(s), 2022, published in Zhurnal Strukturnoi Khimii, 2022, Vol. 63, No. 10, 99529.https://doi.org/10.26902/JSC_id99529

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Gerasimova, D.P., Faizova, R.G., Zakharychev, D.V. et al. 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. J Struct Chem 63, 1616–1628 (2022). https://doi.org/10.1134/S0022476622100080

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