Russian Chemical Bulletin

, Volume 55, Issue 1, pp 1–15

The nature and energy characteristics of intramolecular hydrogen bonds in crystals

  • K. A. Lyssenko
  • M. Yu. Antipin
Reviews

Abstract

The review concerns the results of systematic X-ray diffraction studies of the electron density distribution in the crystals of compounds with strong intramolecular hydrogen bonds N-H...O, O-H...O, O-H...N, and N-H...S. The advantages of the topological analysis of the electron density distribution function in the analysis of the nature and estimation of the H-bond energies directly from experimental data are discussed.

Key words

X-ray diffraction studies quantum chemical calculations topological analysis electron density distribution function intramolecular hydrogen bond N-H...O, O-H...O, O-H...N, and N-H...S proton transfer in crystals 

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References

  1. 1.
    F. N. Keutsch, J. D. Cruzan, and R. J. Saykally, Chem. Rev., 2003, 103, 2533.CrossRefGoogle Scholar
  2. 2.
    P. Gilli and G. Gilli, J. Mol. Struct., 2000, 552, 1.CrossRefGoogle Scholar
  3. 3.
    L. Sobczyk, S. J. Grabowski, and T. M. Krygowski, Chem. Rev., 2005, 105, 3513.CrossRefGoogle Scholar
  4. 4.
    T. Steiner, Angew. Chem., Int. Ed. Engl., 2002, 41, 48.CrossRefGoogle Scholar
  5. 5.
    Yu. V. Zefirov and P. M. Zorkii, Usp. Khim., 1995, 64, 446 [Russ. Chem. Rev., 1995, 64 (Engl. Transl.)].Google Scholar
  6. 6.
    G. Gilli, F. Bellucci, V. Ferretti, and V. Bertolasi, J. Am. Chem. Soc., 1989, 111, 1023.CrossRefGoogle Scholar
  7. 7.
    P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc., 1994, 116, 909.CrossRefGoogle Scholar
  8. 8.
    P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli, J. Am. Chem. Soc., 2000, 122, 10405.Google Scholar
  9. 9.
    P. Gilli, V. Bertolasi, L. Pretto, A. Lycka, and G. Gilli, J. Am. Chem. Soc., 2002, 124, 13554.Google Scholar
  10. 10.
    P. Gilli, V. Bertolasi, L. Pretto, V. Ferretti, and G. Gilli, J. Am. Chem. Soc., 2004, 126, 3845.CrossRefGoogle Scholar
  11. 11.
    P. Gilli, V. Bertolasi, L. Pretto, L. Antonov, and G. Gilli, J. Am. Chem. Soc., 2005, 127, 4943.CrossRefGoogle Scholar
  12. 12.
    K. A. Lyssenko and M. Yu. Antipin, Izv. Akad. Nauk, Ser. Khim., 2001, 400 [Russ. Chem. Bull., Int. Ed., 2001, 50, 418].Google Scholar
  13. 13.
    R. F. W. Bader, Atoms in Molecules. A Quantum Theory, Clarendron Press, Oxford, 1990.Google Scholar
  14. 14.
    Yu. A. Abramov, Acta Crystallogr., 1997, A53, 264.Google Scholar
  15. 15.
    E. Espinosa, E. Molins, and C. Lecomte, Chem. Phys. Lett., 1998, 285, 170.CrossRefGoogle Scholar
  16. 16.
    E. Espinosa, I. Alkorta, I. Rozas, J. Elguero, and E. Molins, Chem. Phys. Lett., 2001, 336, 457.CrossRefGoogle Scholar
  17. 17.
    V. G. Tsirelson, Acta Crystallogr., 2002, B58, 632.Google Scholar
  18. 18.
    E. A. Zhurova, V. G. Tsirelson, A. I. Stash, M. V. Yakovlev, and A. A. Pinkerton, J. Chem. Phys., 2004, B108, 20173.Google Scholar
  19. 19.
    D. A. Kirzhnitts, Zh. Eksp. Teor. Fiz., 1957, 32, 115 [J. Exp. Theor. Phys., 1957, 32 (Engl. Transl.)].Google Scholar
  20. 20.
    A. A. Korlyukov, K. A. Lyssenko, M. Yu. Antipin, V. N. Kirin, E. A. Chernyshev, and S. P. Knyazev, Inorg. Chem., 2002, 41, 5043.CrossRefGoogle Scholar
  21. 21.
    V. Tsirelson and A. Stash, Chem. Phys. Lett., 2002, 351, 142.CrossRefGoogle Scholar
  22. 22.
    V. Tsirelson and A. Stash, Acta Crystallogr., 2002, B58, 780.Google Scholar
  23. 23.
    G. K. H. Madsen, B. B. Iversen, F. K. Larsen, M. Kapon, G. M. Reiser, and F. H. Herbstein, J. Am. Chem. Soc., 1998, 120, 10040.Google Scholar
  24. 24.
    M. Yu. Antipin and K. A. Lyssenko, Abstr. Int. Conf. on Hydrogen Bonding (Moscow, Klyaz’ma, October 6–10, 2004), Moscow, 2004, L11.Google Scholar
  25. 25.
    F. L. Hirshfeld, Acta. Crystallogr., 1976, A32, 239.Google Scholar
  26. 26.
    F. H. Herbstein, B. B. Iversen, M. Kapon, F. K. Larsen, G. K. H. Madsen, and G. M. Reisner, Acta Crystallogr., 1999, B55, 767.Google Scholar
  27. 27.
    R. Boese, M. Yu. Antipin, D. Blaeser, and K. A. Lyssenko, J. Phys. Chem., 1998, B102, 8654.Google Scholar
  28. 28.
    K. A. Lyssenko, D. V. Lyubetsky, and M. Yu. Antipin, Mendeleev Commun., 2003, 60.Google Scholar
  29. 29.
    L. F. Power, K. E. Turner, and F. H. Moore, J. Cryst. Mol. Struct., 1975, 5, 59.CrossRefGoogle Scholar
  30. 30.
    M. Yu. Antipin, K. A. Lysenko, Yu. T. Struchkov, I. A. Odinets, O. I. Artyushin, R. M. Kalyanova, T. A. Mastryukova, and M. I. Kabachnik, Izv. Akad. Nauk, Ser. Khim., 1995, 1520 [Russ. Chem. Bull., 1995, 44, 1460 (Engl. Transl.)].Google Scholar
  31. 31.
    I. L. Odinets, N. M. Vinogradova, O. I. Artyushin, R. M. Kalyaeva, K. A. Lysenko, P. V. Petrovskii, T. A. Mastryukova, and M. I. Kabachnik, Izv. Akad. Nauk, Ser. Khim., 1998, 990 [Russ. Chem. Bull., 1998, 47, 960 (Engl. Transl.)].Google Scholar
  32. 32.
    I. L. Odinets, Ya. A. Vereshchagina, O. I. Artyushin, R. M. Kalyanova, T. A. Mastryukova, E. A. Ishmaeva, G. R. Fattakhova, D. V. Chachkov, and E. G. Yarkova, Izv. Akad. Nauk, Ser. Khim., 2003, 611 [Russ. Chem. Bull., Int. Ed., 2003, 52, 638].Google Scholar
  33. 33.
    K. A. Lysenko, D. V. Lyubetskii, M. Yu. Antipin, and I. L. Odinets, Izv. Akad. Nauk, Ser. Khim., 2005, 2406 [Russ. Chem. Bull., Int. Ed., 2005, 54, No. 11, 2484].Google Scholar
  34. 34.
    A. Filarowski, T. Glowiaka, and A. Koll, J. Mol. Struct., 1999, 484, 75.CrossRefGoogle Scholar
  35. 35.
    A. Filarowski, A. Koll, and T. Glowiak, Monat. Chem., 1999, 130, 1097.Google Scholar
  36. 36.
    A. Filarowski, A. Koll, and T. Glowiak, J. Chem. Soc., Perkin Trans. 2, 2002, 835.Google Scholar
  37. 37.
    V. Rozenberg, T. Danilova, E. Sergeeva, E. Vorontsov, Z. Starikova, K. Lyssenko, and Yu. Belokon, Eur. J. Org. Chem., 2000, 19, 3295.CrossRefGoogle Scholar
  38. 38.
    K. Wozniak, P. R. Mallinson, G. T. Smith, C. C. Wilson, and E. Grech, J. Phys. Org. Chem., 2003, 16, 764.CrossRefGoogle Scholar
  39. 39.
    P. M. Dominiak, E. Grech, G. Barr, S. Teat, P. R. Mallinson, and K. Wozniak, Chem. Eur. J., 2003, 9, 963.CrossRefGoogle Scholar
  40. 40.
    K. A. Lyssenko, O. R. Prokopenko, V. N. Nesterov, T. V. Timofeeva, and M. Yu. Antipin, Mendeleev. Commun., 2005, 135.Google Scholar
  41. 41.
    V. A. Kozlov, I. L. Odinets, K. A. Lyssenko, S. G. Churusova, S. V. Yarovenko, P. V. Petrovskii, and T. A. Mastryukova, Heteroatom. Chem., 2005, 16, 159.CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, Inc. 2006

Authors and Affiliations

  • K. A. Lyssenko
    • 1
  • M. Yu. Antipin
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation

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