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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 11, pp 1631–1639 | Cite as

Spectral and Quantum-Chemical Study of Nonequivalence of Methylene Protons in 1,4-Dihydropyridine Derivatives*

  • M. PetrovaEmail author
  • R. Muhamadejev
  • A. Chesnokov
  • B. Vigante
  • B. Cekavicus
  • A. Plotniece
  • G. Duburs
  • E. Liepinsh
Article

Structural characteristics of 1,4-dihydropyridines influencing the nonequivalence of the diastereotopic methylene protons in substituents at positions 2 and 6 were studied. The combined effect of magnetically anisotropic groups and intramolecular hydrogen bonds leads to a considerable difference in the chemical shifts of the methylene protons of the AB system. The unusual reversible temperature evolution of these proton signals in monocyclic 1,4-dihydropyridines is associated with two simultaneous conformational processes. It was estimated that the energetically most favorable conformations are stabilized by an intramolecular СН⋯О hydrogen bond.

Keywords

1,4-dihydropyridines 1Н NMR spectroscopy hydrogen bond nonequivalence of methylene protons quantum-chemical calculations 

Notes

This project was supported by the Latvian National Research Program “Biomedicine”.

References

  1. 1.
    N. Edraki, A. R. Mehdipour, M. Khoshneviszadeh, and R. Miri, Drug Discovery Today, 14, 1058 (2009).CrossRefGoogle Scholar
  2. 2.
    D. J. Triggle, Biochem. Pharmacol., 78, 217 (2009).CrossRefGoogle Scholar
  3. 3.
    I. P Skrastins, V. V. Kastron, B. S. Cekavicus, A. E. Sausins, R. M. Zolotoyabko, and G. J. Duburs, Khim. Geterotsikl. Soedin., 1230 (1991). [Chem. Heterocycl. Compd., 27, 989 (1991).]Google Scholar
  4. 4.
    A. Urtti, Z. Hyvonen, A. Plotniece, N. Makarova, I. Reine, G. Tirzitis, B. Vigante, B. Cekavicus, A. Shmidlers, A. Krauze, R. Zhalubovskis, G. Duburs, M. Turunen, S. Yla-Herttuala, I. Jaaskelainen, and M.-R. Toppinen, US Pat. Appl. 20030064954.Google Scholar
  5. 5.
    K. Pajuste, A. Plotniece, K. Kore, L. Intenberga, B. Cekavicus, D. Kaldre, G. Duburs, and A. Sobolev, Cent. Eur. J. Chem., 9, 143 (2011).CrossRefGoogle Scholar
  6. 6.
    A. Plotniece, K. Pajuste, D. Kaldre, B. Cekavicus, B. Vigante, B. Turovska, S. Belyakov, A. Sobolev, and G. Duburs, Tetrahedron, 65, 8344 (2009).CrossRefGoogle Scholar
  7. 7.
    M. Petrova, R. Muhamadejev, B. Vigante, B. Cekavicus, A. Plotniece, G. Duburs, and E. Liepinsh, Molecules, 16, 8041 (2011).CrossRefGoogle Scholar
  8. 8.
    T. Yamada, H. Miki, I. Aoki, and A. Otomo, Opt. Mater. (Amsterdam, Neth.), 35, 2194 (2013).Google Scholar
  9. 9.
    W. Lian, Y. Lin, M. Wang, C. Yang, and J. Wang, CrystEngComm, 15, 3885 (2013).CrossRefGoogle Scholar
  10. 10.
    T. Yamada, I. Aoki, H. Miki, C. Yamada, and A. Otomo, Mater. Chem. Phys., 139, 699 (2013).CrossRefGoogle Scholar
  11. 11.
    M. Abdoli-Senejani, A. A. Taherpour, H. R. Memarian, and M. Khosravani, Struct. Chem., 24, 191 (2012).CrossRefGoogle Scholar
  12. 12.
    M. Thenmozhi, T. Kavitha, B. P. Reddy, V. Vijayakumar, and M. N. Ponnuswamy, Acta Crystallogr., Sect. E: Struct. Rep. Online, 65, o2795 (2009).Google Scholar
  13. 13.
    M. Mahendra, B. H. Doreswamy, P. Adlakha, K. Raval, A. Shah, S. M. Anandalwar, and J. S. Prasad, Anal. Sci.: X-Ray Struct. Anal. Online, 21, x35 (2005).Google Scholar
  14. 14.
    R. Fossheim, Acta Chem. Scand., Ser. B, B41, 581 (1987).CrossRefGoogle Scholar
  15. 15.
    I. P. Sekacis, E. E. Liepinsh, and G. J. Duburs, Izv. Akad. Nauk LatvSSR, Ser. Khim., 1, 111 (1979).Google Scholar
  16. 16.
    C. Giacovazzo, H. L. Monaco, G. Artioli, D. Viterbo, G. Ferraris, G. Gilli, G. Zanotti, and M. Catti, Fundamentals of Crystallography, 2nd ed., Oxford University Press, Oxford (2002), p. 848.Google Scholar
  17. 17.
    A. Ahmed, R. A. Bragg, J. Clayden, L. W. Lai, C. McCarthy, J. H. Pink, N. Westlund, and S. A. Yasin, Tetrahedron, 54, 13277 (1998).CrossRefGoogle Scholar
  18. 18.
    Jaguar, Version 8.0, Schrodinger, LLC, New York (2011).Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • M. Petrova
    • 1
    Email author
  • R. Muhamadejev
    • 1
  • A. Chesnokov
    • 1
  • B. Vigante
    • 1
  • B. Cekavicus
    • 1
  • A. Plotniece
    • 1
  • G. Duburs
    • 1
  • E. Liepinsh
    • 1
  1. 1.Latvian Institute of Organic SynthesisRigaLatvia

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