Skip to main content
SpringerLink
Log in

A thermodynamic study of reactions of amino acids with crown ethers in nonaqueous media as examples of guest—host molecular complex formation

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Our findings and the literature data on the effect of binary aqueous organic solvents on the enthalpy and entropy of molecular complexation reactions of 18-crown-6 with glycine, D, L-alanine, and L-phenylalanine and on the stability of the resulting complexes were reviewed. The relationships between the thermodynamic parameters of the complexation reactions and the reactant solvation were analyzed to reveal the key factors that are crucial for the stability of the complexes and the increasing exothermicity of the processes under study in water—ethanol, water—DMSO, and water—acetone. The changes in the stability of 18-crown-6 complexes with amino acids were assumed to be predicted from the Gibbs energy changes in the transsolvation of the amino acids. This criterion was proposed as a basic thermodynamic parameter for estimating the changes in the stability of 18-crown-6 complexes with peptides and ammoniumtype cations (structurally related to amino acids) when the composition of the binary aqueous organic solvent is varied.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, 1995, 271 pp.

    Book  Google Scholar 

  2. G. A. Krestov, Termodinamika ionnykh protsessov v rastvorakh [The Thermodynamics of Ionic Processes in Solutions], Khimiya, Leningrad, 1984, 272 pp. (in Russian).

    Google Scholar 

  3. M. Hiraoka, Crown Compounds: Their Characteristics and Applications, Elsevier Science Publishers, 1982.

    Google Scholar 

  4. J. L. Atwood, J. E. D. Davies, D. D. MacNicol, F. Vögtle, Comprehensive Supramolecular Chemistry, Elsevier, Oxford, 1996, 535 pp.

    Google Scholar 

  5. M. Jozwiak, A. Warezakowska, J. Therm. Anal. Calorim.; DOI 10.1007/s10973-015-4630-0.

  6. M. Reis, N. Nuñes, R. Elvas-Leitão, F. Martins, Thermochim. Acta, 2015, 604, 140.

    Article  CAS  Google Scholar 

  7. S. N. Bondarev, N. V. Bondarev, Vistn. Kharkiv. Natl. Univ., Khim. [Bulletin of the Kharkiv National University, Chemistry], 2010, 19, 70 (in Ukrainian).

    Google Scholar 

  8. V. P. Solovév, D. Sc. (Chem.) Thesis, A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, 2007, 350 pp. (in Russian).

    Google Scholar 

  9. V. N. Glushko, L. I. Blokhina, N. Yu. Sadovskaya, L. A. Pevtsova, S. K. Beluś, Russ. J. Gen. Chem. (Engl. Transl.), 2014, 84, 2079 [Zh. Obshch. Khim., 2014, 84, 1780].

    Article  CAS  Google Scholar 

  10. E. N. Ushakov, M. V. Alfimov, S. P. Gromov, Russ. Chem. Rev., 2008, 77, 39 [Usp. Khim., 2008, 77, 39].

    Article  CAS  Google Scholar 

  11. A. N. Timonin, Ph.D. (Biol.) Thesis, K. I. Skryabin Moscow State Academy of Veterinary Medicine and Biotechnology, Moscow, 2011, 125 pp. (in Russian).

    Google Scholar 

  12. N. N. Popova, Ya. I. Korenman, T. A. Kuchmenko, Sovrem. Naukoemkie Tekhnol. Khim. Nauki [Modern High Technologies. Chemical Sciences], 2007, 5, 19 (in Russian).

    Google Scholar 

  13. A. I. Aleksandrov, T. V. Pashkova, A. V. Pyatunin, I. V. Lipunov, Zhidkie Krist. Ikh Prakt. Ispolź. [Liquid Crystals and Their Practical Applications], 2008, 26, 73 (in Russian).

    Google Scholar 

  14. N. V. Borzenkova, I. A. Veselova, T. N. Shekhovtsova, Vestn. Mosk. Univ., Ser. 2: Khim., 2012, 5, 291 [Moscow Univ. Chem. Bull. (Engl. Transl.), 2012, 5].

    Google Scholar 

  15. M. A. Katkova, G. S. Zabrodina, M. S. Muravyeva, A. A. Khrapichev, M. A. Samsonov, G. K. Fukin, S. Yu. Ketkov, Inorg. Chem. Commun., 2015, 52, 31.

    Article  CAS  Google Scholar 

  16. M. Fang, T. Wang, Inorg. Chem. Commun., 2014, 46, 184.

    Article  CAS  Google Scholar 

  17. M. Sutradhar, M. F. C. Guedes da Silva, A. J. L. Pombeiro, Inorg. Chem. Commun., 2013, 30, 42.

    Article  CAS  Google Scholar 

  18. G. Mezei, C. M. Zaleski, V. L. Pecoraro, Chem. Rev., 2007, 107, 4933.

    Article  CAS  Google Scholar 

  19. O. V. Kulikov, N. Yu. Kornilova, Russ. J. Phys. Chem. (Engl. Transl.), 1996, 70, 1959 [Zh. Fiz. Khim., 1996, 70, 2119].

    Google Scholar 

  20. O. V. Kulikov, I. V. Terekhova, Russ. J. Coord. Chem. (Engl. Transl.), 1997, 23, 889 [Koord. Khim., 1997, 23, 946].

    CAS  Google Scholar 

  21. O. V. Kulikov, I. V. Terekhova, Russ. J. Coord. Chem. (Engl. Transl.), 1998, 24, 373 [Koord. Khim., 1998, 24, 395].

    CAS  Google Scholar 

  22. O. V. Kulikov, P. V. Lapshev, I. V. Terekhova, Russ. J. Phys. Chem. (Engl. Transl.), 1998, 72, 632 [Zh. Fiz. Khim., 1998, 72, 725].

    Google Scholar 

  23. O. V. Kulikov, I. V. Terekhova, Russ. J. Coord. Chem. (Engl. Transl.), 1998, 24, 821 [Koord. Khim., 1998, 24, 878].

    CAS  Google Scholar 

  24. I. V. Terekhova, O. V. Kulikov, Russ. Chem. Bull. (Engl. Transl.), 1999, 48, 2259 [Izv. Akad. Nauk, Ser. Khim., 1999, 2285].

    Article  CAS  Google Scholar 

  25. I. V. Terekhova, O. V. Kulikov, A. V. Agafonov, Russ. J. Gen. Chem. (Engl. Transl.), 2003, 73, 312 [Zh. Obshch. Khim., 2003, 73, 336].

    Article  CAS  Google Scholar 

  26. I. V. Terekhova, O. V. Kulikov, V. P. Barannikov, Russ. J. Gen. Chem. (Engl. Transl.), 2004, 74, 1213 [Zh. Obshch. Khim., 2004, 74, 1313].

    Article  CAS  Google Scholar 

  27. O. V. Kulikov, I. V. Terekhova, R. S. Kumeev, G. A. Al´per, Russ. J. Phys. Chem. (Engl. Transl.), 2004, 78, 1488 [Zh. Fiz. Khim., 2004, 78, 1694].

    Google Scholar 

  28. H.-J. Buschmann, L. Mutihac, in Thermodynamics of Amino Acid and Protein Solutions, Ed. J. Tsurko, W. Kunz, Transworld Research Network, Kerala, India, 2010, 151 pp.

  29. H.-J. Buschmann, L. Mutihac, K. Jansen, J. Inclusion Phenom. Macrocycl. Chem., 2001, 39, 1.

    Article  CAS  Google Scholar 

  30. H.-J. Buschmann, L. Mutihac, J. Inclusion Phenom. Macrocycl. Chem., 2002, 42, 193.

    Article  CAS  Google Scholar 

  31. L. Mutihac, H.-J. Buschmann, K. Jansen, A. Wego, Mater. Sci. Eng. C, 2001, 18, 259.

    Article  Google Scholar 

  32. H.-J. Buschmann, E. Schollmeyer, L. Mutihac, Thermochim. Acta, 1998, 316, 189.

    Article  CAS  Google Scholar 

  33. A. F. Danil de Namor, M. C. Ritt, D. F. V. Lewis, M. J. Schwing-Weill, F. A. Neu, Pure Appl. Chem., 1991, 63, 1435.

    CAS  Google Scholar 

  34. A. F. Danil de Namor, M. C. Ritt, M. J. Schwing-Weill, F. Arnaud-Neu, D. F. V. Lewis, J. Chem. Soc., Faraday Trans., 1991, 87, 3231.

    Article  CAS  Google Scholar 

  35. A. F. Danil de Namor, R. Traboulssi, D. F. V. Lewis, J. Am. Chem. Soc., 1990, 112, 8442.

    Article  CAS  Google Scholar 

  36. A. F. Danil de Namor, M. C. Ritt, M.-J. Schwing-Weill, F. Arnaud-Neu, D. F. V. Lewis, J. Chem. Soc., Chem. Commun., 1990, 116.

    Google Scholar 

  37. M. Czekalla, H. Stephan, B. Habermann, J. Trepte, K. Gloe, F. P. Schmidtchen, Thermochim. Acta, 1998, 313, 137.

    Article  CAS  Google Scholar 

  38. V. A. Shormanov, V. A. Sharnin, in Dostizheniya i problemy teorii sol´vatatsii: strukturno-termodinamicheskie aspekty [Achievements and Problems in Solvation Theory: Structural and Thermodynamic Aspects], Ed. A. M. Kutepov, Nauka, Moscow, 1998, 172 (in Russian).

  39. V. A. Sharnin, Zh. Obshch. Khim., 1994, 64, 1914 [Russ. J. Gen. Chem. (Eng. Transl.), 1994, 64].

    Google Scholar 

  40. V. A. Sharnin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2005, 48, 44 (in Russian).

    CAS  Google Scholar 

  41. V. A. Sharnin, Russ. J. Gen. Chem. (Engl. Transl.), 1999, 69, 1368 [Zh. Obshch. Khim., 1999, 69, 1424].

    CAS  Google Scholar 

  42. V. A. Sharnin, Russ. J. Gen. Chem. (Engl. Transl.), 2001, 71, 1373 [Zh. Obshch. Khim., 2001, 71, 1452].

    Article  CAS  Google Scholar 

  43. V. A. Sharnin, Russ. J. Coord. Chem. (Engl. Transl.), 1996, 22, 394 [Koord. Khim., 1996, 22, 418].

    Google Scholar 

  44. I. Wadsö, Thermochim. Acta, 2002, 394, 305.

    Article  Google Scholar 

  45. V. P. Vasilév, V. A. Borodin, E. V. Kozlovskii, Primenenie EVM v khimiko-analiticheskikh raschetakh [Computer-Aided Calculations in Analytical Chemistry], Vysshaya Shkola, Moscow, 1993, 112 pp. (in Russian).

    Google Scholar 

  46. V. A. Borodin, E. V. Kozlovskii, V. P. Vasilév, Zh. Neorg. Khim., 1982, 27, 2169 [J. Inorg. Chem. USSR (Engl. Transl.), 1982, 27].

    CAS  Google Scholar 

  47. O. V. Kulikov, G. A. Krestov, W. Zielenkiewicz, J. Solution Chem., 1995, 24, 1155.

    Article  CAS  Google Scholar 

  48. O. V. Kulikov, G. A. Krestov, Pure Appl. Chem., 1995, 67, 1103.

    Article  CAS  Google Scholar 

  49. T. R. Usacheva, I. V. Chernov, V. A. Sharnin, E. Matteoli, I. V. Terekhova, R. S. Kumeev, Chem. Phys. Lett., 2012, 543, 153.

    Article  Google Scholar 

  50. E. Matteoli, L. Lepori, T. R. Usacheva, V. A. Sharnin, J. Therm. Anal. Calorim., 2009, 97, 811.

    Article  CAS  Google Scholar 

  51. T. R. Usacheva, V. A. Sharnin, E. Matteoli, Russ. J. Phys. Chem. (Engl. Transl.), 2011, 85, 1898 [Zh. Fiz. Khim., 2011, 85, 2038].

    Article  CAS  Google Scholar 

  52. T. R. Usacheva, V. A. Sharnin, I. V. Chernov, E. Matteoli, J. Therm. Anal. Calorim., 2013, 112, 983.

    Article  CAS  Google Scholar 

  53. T. R. Usacheva, I. A. Kuźmina, V. A. Sharnin, I. V. Chernov, E. Matteoli, Russ. J. Phys. Chem. (Engl. Transl.), 2012, 86, 36 [Zh. Fiz. Khim., 2012, 86, 42].

    Article  CAS  Google Scholar 

  54. T. R. Usacheva, I. A. Kuźmina, V. A. Sharnin, I. V. Chernov, E. Matteoli, Russ. J. Phys. Chem. (Engl. Transl.), 2012, 86, 1064 [Zh. Fiz. Khim., 2012, 86, 1179].

    Article  CAS  Google Scholar 

  55. T. R. Usacheva, I. V. Chernov, V. A. Sharnin, S. I. Voronina, E. Matteoli, J. Therm. Anal. Calorim., 2013, 112, 399.

    Article  CAS  Google Scholar 

  56. T. R. Usacheva, V. A. Sharnin, I. V. Chernov, Russ. J. Phys. Chem. (Engl. Transl.), 2013, 87, 204 [Zh. Fiz. Khim., 2013, 87, 225].

    Article  CAS  Google Scholar 

  57. K. Sharp, Protein Sci., 2001, 10, 661.

    Article  CAS  Google Scholar 

  58. J. D. Chodera, D. L. Mobley, Annu. Rev. Biophys., 2013, 42, 121.

    Article  CAS  Google Scholar 

  59. Y. Ionoue, T. Hakushi, J. Chem. Soc., Perkin Trans. 2, 1985, 935.

    Google Scholar 

  60. O. V. Kulikov, P. V. Lapshev, in Biologicheski aktivnye veshchestva v rastvorakh: struktura, termodinamika, reaktsionnaya sposobnost [Biologically Active Compounds in Solutions: Structures, Thermodynamics, and Reactivities], Ed. A. M. Kutepov, Nauka, Moscow, 2001, p. 184 (in Russian).

  61. A. Yu. Tsivadze, A. A. Varnek, V. E. Khutorskii, Koordinatsionnye soedineniya metallov s kraun-ligandami [Coordination Compounds of Metals with Crown Ligands], Nauka, Moscow, 1991, 397 pp. (in Russian).

    Google Scholar 

  62. I. V. Terekhova, P. V. Lapshev, O. V. Kulikov, Russ. J. Phys. Chem. (Engl. Transl.), 200, 74, 1830 [Zh. Fiz. Khim., 2000, 74, 2011].

  63. I. V. Terekhova, P. V. Lapshev, O. V. Kulikov, Russ. J. Coord. Chem. (Engl. Transl.), 2003, 29, 73 [Koord. Khim., 2003, 29, 78].

    Article  CAS  Google Scholar 

  64. T. R. Usacheva, I. A. Kuźmina, M. O. Dzhumasheva, N. S. Sidorenko, V. A. Sharnin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2010, 53, 51 (in Russian).

    CAS  Google Scholar 

  65. T. R. Usacheva, I. A. Kuźmina, V. A. Sharnin, N. S. Sidorenko, S. I. Voronina, Russ. J. Phys. Chem. (Engl. Transl.), 2011, 85, 952 [Zh. Fiz. Khim., 2011, 85, 1047].

    Article  CAS  Google Scholar 

  66. B. P. Dey, S. C. Lahiri, Indian J. Chem., 1986, 25A, 136.

    CAS  Google Scholar 

  67. Zh. F. Gesse, V. A. Isaeva, V. A. Sharnin, Russ. J. Phys. Chem. (Engl. Transl.), 2010, 84, 329 [Zh. Fiz. Khim., 2010, 84, 385].

    Article  CAS  Google Scholar 

  68. T. R. Usacheva, S. F. Ledenkov, V. A. Sharnin, A. Grzejdziak, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2000, 43, 87 (in Russian).

    CAS  Google Scholar 

  69. T. R. Usacheva, I. A. Kuźmina, V. A. Sharnin, I. V. Chernov, E. Matteoli, Russ. J. Phys. Chem. (Engl. Transl.), 2011, 85, 948 [Zh. Fiz. Khim., 2011, 85, 1043].

    Article  CAS  Google Scholar 

  70. M. Jozwiak, J. Therm. Anal. Calorim., 2010, 101, 1039.

    Article  CAS  Google Scholar 

  71. M. Jozwiak, J. Mol. Liq., 2003, 107, 169.

    Article  CAS  Google Scholar 

  72. V. I. Smirnov, V. G. Badelin, Russ. J. Phys. Chem. (Engl. Transl.), 2003, 77, 713 [Zh. Fiz. Khim., 2003, 77, 803].

    Google Scholar 

  73. V. I. Smirnov, V. G. Badelin, Biophysics (Engl. Transl.), 2004, 49, 375 [Biofizika, 2004, 49, 395].

    Google Scholar 

  74. V. I. Smirnov, I. N. Mezhevoi, V. G. Badelin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2003, 46, 90 (in Russian).

    CAS  Google Scholar 

  75. V. I. Smirnov, I. N. Mezhevoi, V. G. Badelin, Russ. J. Phys. Chem. (Engl. Transl.), 2004, 78, 214 [Zh. Fiz. Khim., 2004, 78, 280].

    Google Scholar 

  76. V. I. Smirnov, I. N. Mezhevoi, V. G. Badelin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol. [Bulletin of High Schools, Chemistry and Chemical Technology], 2004, 47, 38 (in Russian).

    Google Scholar 

  77. V. I. Smirnov, V. G. Badelin, I. N. Mezhevoi, Russ. J. Phys. Chem. (Engl. Transl.), 2006, 80, 672 [Zh. Fiz. Khim., 2006, 80, 780].

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Ivanovo State University of Chemistry and Technology, 7 Sheremetevskii prosp., 153000, Ivanovo, Russian Federation

    T. R. Usacheva & V. A. Sharnin

  2. G. A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 1 ul. Akademicheskaya, 153045, Ivanovo, Russian Federation

    V. A. Sharnin

Authors
  1. T. R. Usacheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. A. Sharnin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to V. A. Sharnin.

Additional information

Based on the materials of the XXVI International Chugaev Conference on Coordination Chemistry (October 6—10, 2014, Kazan, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2536—2544, November, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Usacheva, T.R., Sharnin, V.A. A thermodynamic study of reactions of amino acids with crown ethers in nonaqueous media as examples of guest—host molecular complex formation. Russ Chem Bull 64, 2536–2544 (2015). https://doi.org/10.1007/s11172-015-1189-7

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-1189-7

Key words

Search

Navigation