Skip to main content
SpringerLink
Log in

FROM THE STEREOCHEMISTRY OF A MOLECULE TO THE STEREOCHEMISTRY OF A CRYSTAL: CHIRAL CRYSTALLIZATION OF ENDO-ISOMERS COMPARED WITH CENTROSYMMETRIC CRYSTALLIZATION OF EXO-ISOMERS OF THIIRANE AND OXIRANE DERIVATIVES OF PHENYL- SUBSTITUTED SEVEN-MEMBERED ACETAL

  • Published:
Journal of Structural Chemistry Aims and scope Submit manuscript

Abstract

The chiral type of crystallization of endo-isomers of 4-phenyl-3,5,8-trioxabicyclo[5.1.0]octane and 4-phenyl-3,5-dioxa-8-thiabicyclo[5.1.0]octane and the formation of racemic crystals by molecules corresponding exo-isomers are established. The relationship between the structural organization of molecules and the stereochemical type of intermolecular interactions and the formation of different types of crystals is analyzed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

REFERENCES

  1. D. K. Kondepudi, J. Laudadio, and K. Asakura. J. Am. Chem. Soc., 1999, 121, 1448. https://doi.org/10.1021/ja983418u

    Article  CAS  Google Scholar 

  2. B. S. Green, M. Lahav, and D. Rabinovich. Acc. Chem. Res., 1979, 12, 191. https://doi.org/10.1021/ar50138a001

    Article  CAS  Google Scholar 

  3. M. Sakamoto, A. Unosawa, S. Kobaru, K. Fujita, T. Mino, and T. Fujita. Chem. Commun., 2007, 34, 3586. https://doi.org/10.1039/b706426h

    Article  Google Scholar 

  4. A. Jaques, A. Collet, and S. H. Wilen. Enantiomers, Racemates and Resolutions. New York: Wiley, 1981.

  5. B. S. Green, M. Lahav, and D. Rabinovich. Acc. Chem. Res., 1979, 12, 191. https://doi.org/10.1021/ar50138a001

    Article  CAS  Google Scholar 

  6. L. Leiserowitz and M. Weinstein. Acta Crystallogr., Sect. B: Struct. Sci., 1975, 31, 1463. https://doi.org/

    Article  Google Scholar 

  7. L. Addadi and M. Lahav. Pure Appl. Chem., 1979, 51, 1269. https://doi.org/10.1351/pac197951061269

    Article  CAS  Google Scholar 

  8. E. L. Eliel, S. H. Wilen, and L. N. Mander. Stereochemistry of Organic Compounds. New York: Wiley, 1994.

  9. I. J. Bruno, J. C. Cole, P. R. Edgington, M. Kessler, C. F. Macrae, P. McCabe, J. Pearson, and R. Taylor. Acta Crystallogr., Sect. B: Struct. Sci., 2002, 58, 389. https://doi.org/10.1107/S0108768102003324

    Article  Google Scholar 

  10. T. Matsuura and H. Koshima. J. Photochem. Photobiol. C, 2005, 6, 7. https://doi.org/10.1016/j.jphotochemrev.2005.02.002

    Article  CAS  Google Scholar 

  11. A. Matsumoto, S. Tsuchiya, Y. Hagiwara, K. Ishikawa, H. Koshima, T. Asahi, and K. Soai. Chem. Lett., 2016, 45, 526. https://doi.org/10.1246/cl.160114

    Article  CAS  Google Scholar 

  12. O. A. Lodochnikova, L. Z. Latypova, R. M. Khakimov, A. R. Kurbangalieva, D. B. Krivolapov, and I. A. Litvinov. J. Struct. Chem., 2013, 54(1), 213. https://doi.org/10.1134/S0022476613010356

    Article  CAS  Google Scholar 

  13. R. S. Pavelyev, S. G. Gnevashev, R. M. Vafina, O. I. Gnezdilov, A. B. Dobrynin, S. A. Lisovskaya, L. E. Nikitina, and E. N. Klimovitskii. Mendeleev Commun., 2012, 22, 127. https://doi.org/10.1016/j.mencom.2012.05.003

    Article  CAS  Google Scholar 

  14. V. V. Gavrilov, A. B. Dobrynin, R. M. Vafina, A. E. Klimovitskii, V. Yu. Fedorenko, O. N. Kataeva, E. A. Berdnikov, I. A. Litvinov, Yu. G. Shtyrlin, R. Fröhlich, and E. N. Klimovitskii. J. Mol. Struct., 2007, 837, 79. https://doi.org/10.1016/j.molstruc.2006.09.033

    Article  CAS  Google Scholar 

  15. APEX2 (Version 2.1), SAINTPlus. Data Reduction and Correction Program (Version 7.31A). Madison, Wisconsin, USA: Bruker AXS, 2006.

  16. G. M. Sheldrick. SADABS. Madison, WI, USA: Bruker AXS, 1997.

  17. G. M. Sheldrick. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3. https://doi.org/10.1107/s2053273314026370

    Article  Google Scholar 

  18. G. M. Sheldrick. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3. https://doi.org/10.1107/s2053229614024218

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  20. A. L. Spek. Acta Crystallogr., Sect. D, 2009, 65, 148-155. https://doi.org/10.1107/S090744490804362X

    Article  CAS  Google Scholar 

  21. C. F. Macrae, I. Sovago, S. J. Cottrell, P. T. A. Galek, P. McCabe, E. Pidcock, M. Platings, G. P. Shield, J. S. Stevens, M. Towler, and P. A. Wood. J. Appl. Crystallogr., 2020, 53, 226. https://doi.org/10.1107/S1600576719014092

    Article  CAS  Google Scholar 

  22. V. Y. Fedorenko, O. A. Lodochnikova, A. S. Petukhov, O. N. Kataeva, I. A. Litvinov, Y. G. Shtyrlin,and E. N. Klimovitskii, J. Mol. Struct., 2003, 644, 89. https://doi.org/10.1016/S0022-2860(02)00478-7

    Article  CAS  Google Scholar 

  23. G. R. Clark and G. J. Palenik. J. Chem. Soc., Perkin Trans. 2, 1973, 194. https://doi.org/10.1039/p29730000194

    Article  Google Scholar 

  24. R. M. Vafina, O. N. Kataeva, I. A. Litvinov, G. N. Sergeeva, and E. N. Klimovitskii. Russ. J. Org. Chem., 1993, 29, 1567.

  25. Y. G. Shtyrlin, V. Y. Fedorenko, O. N. Kataeva, I. A. Litvinov, A. T. Gubaidullin, D. B. Krivolapov,and E. N. Klimovitsky. Russ. J. Gen. Chem., 1998, 68, 1793.

  26. P. Camilleri, D. Munro, K. Weaver, D. J. Williams, H. S. Rzepa, and A. M. Z. Slawin. J. Chem. Soc., Perkin Trans. 2, 1989, 1265. https://doi.org/10.1039/P29890001265

    Article  Google Scholar 

  27. A. E. Klimovitskii, E. E. Zvereva, G. A. Chmutova, A. B. Dobrynin, V. Yu. Fedorenko, Yu. G. Shtyrlin, I. A. Litvinov, T. V. Bulgina, and E. N. Klimovitskii. J. Mol. Struct., 2007, 828, 147. https://doi.org/10.1016/j.molstruc.2006.05.045

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

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

    D. P. Gerasimova & O. A. Lodochnikova

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

    R. S. Pavelyev

Authors
  1. D. P. Gerasimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. S. Pavelyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. O. A. Lodochnikova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. P. Gerasimova.

Ethics declarations

The authors declare that they have no conflict of interests.

Additional information

Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 11, pp. 1807-1815.https://doi.org/10.26902/JSC_id81931

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gerasimova, D.P., Pavelyev, R.S. & Lodochnikova, O.A. FROM THE STEREOCHEMISTRY OF A MOLECULE TO THE STEREOCHEMISTRY OF A CRYSTAL: CHIRAL CRYSTALLIZATION OF ENDO-ISOMERS COMPARED WITH CENTROSYMMETRIC CRYSTALLIZATION OF EXO-ISOMERS OF THIIRANE AND OXIRANE DERIVATIVES OF PHENYL- SUBSTITUTED SEVEN-MEMBERED ACETAL. J Struct Chem 62, 1694–1702 (2021). https://doi.org/10.1134/S0022476621110056

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0022476621110056

Keywords

Search

Navigation