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Formation of molecular complexes between 18-crown-6 and amino acids in aqueous-organic media

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Abstract

Data on the effect of aqueous-organic solvent composition on molecular complexes formation of 18-crown-6 with glycine, D,L-alanine, and L-phenylalanine have been generalized. The inncrease in ethanol, dimethylsulfoxide, or acetone fraction enhances the complexes stability. Amino acid solvation gives the major impact on the Gibbs free energy of complexes formation. It was demonstrated that stability of 18-crown-6 complexes with amino acids could be predicted basing on changes of the amino acid solvation state.

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References

  1. Pedersen, K.D. and Frensdorf, Kh.K., Usp. Khim., 1973, vol. 42, no. 3, p. 492.

    Google Scholar 

  2. Pedersen, Ch., Otkrytie kraun-efirov. Novoe v zhizni, nauke i tehnike. Seriya “Khimiya” (Discovery of Crown Ethers. New in Life, Science, and Technology. Series “Chemistry”), Moscow: Znanie, 1989, no. 1, p. 3.

    Google Scholar 

  3. Hiraoka, M., Crown Compounds: Their Characteristics and Applications, Amst, 1982.

    Google Scholar 

  4. Kram, D., Poluchenie molekulyarnykh kompleksov tipa “gost’-hozyain.” Novoe v zhizni, nauke i tehnike. Seriya “Khimiya” (Production of Molecular Complexes of the “Guest-Host.” New in Life, Science, and Technology. Series “Chemistry”), Moscow: Znanie, 1989, no. 1, p. 3.

    Google Scholar 

  5. Davydova, S.L., Udivitel’nye makrortsikly (An Amazing Macrocycles), Leningrad: Khimiya, 1989.

    Google Scholar 

  6. Dietrich, B., Viout, P., and Lehn, J.-M., Macrocyclic Chemistry, Weinheim: VCH Verlagsgesellschaft mbH., 1993.

    Google Scholar 

  7. Lehn, J.-M., Supramolecular Chemistry: Concepts and Perspectives, VCH Weinheim, 1995.

    Book  Google Scholar 

  8. Duhovich, F.S., Darhovskij, M.B., Gorbatova, E.N., and Kurochkin, V.K., Molekulyarnoe uznavanie: farmakologicheskie aspekty (Molecular Recognition: Pharmacological Aspects), Moscow: Meditsina, 2004.

    Google Scholar 

  9. Steed, J.W. and Atwood, J.L., Supramolecular Chemistry, Wiley, 2009.

    Book  Google Scholar 

  10. Macrocyclic Chemistry: New Research Developments, Fitzpatrick, D.W. and Ulrich, H.J., Eds., New York: Nova Science Publishers Inc., 2010.

    Google Scholar 

  11. Ushakov, E.N., Alfimov, M.V., and Gromov, S.P., Ross. Nanotehnol., 2008, vol. 3, nos. 1–2, p. 42.

    Google Scholar 

  12. Aleksandrov, A.I., Pashkova, T.V., Pyatunin, A.V., and Lipunov, I.V., Zhidkie kristally i ikh prakticheskoe ispol’zovanie, 2008, no. 4(26), p. 73.

    Google Scholar 

  13. Krestov, G.A., Termodinamika ionnykh protsessov v rastvorakh (Thermodynamics of Ionic Processes in Solutions), Leningrad: Khimiya, 1984.

    Google Scholar 

  14. Terekhova, I.V., Parfenyuk, E.V., and Kulikov, O.V., J. Therm. Anal. Calorim., 2002, vol. 68, p. 185.

    Article  CAS  Google Scholar 

  15. Kulikov, O.V., Lapshev, P.V., and Terekhova, I.V., Russ. J. Phys. Chem., A, 1998, vol. 72, no. 4, p. 632.

    Google Scholar 

  16. Kulikov, O.V. and Terekhova, I.V., Russ. J. Coord. Chem., 1998, vol. 24, no. 5, p. 373.

    CAS  Google Scholar 

  17. Kulikov, O.V. and Terekhova, I.V., Russ. J. Coord. Chem., 1997, vol. 23, no. 12, p. 889.

    CAS  Google Scholar 

  18. Kulikov, O.V. and Terekhova, I.V., Russ. J. Coord. Chem., 1998, vol. 24, no. 11, p. 821.

    CAS  Google Scholar 

  19. Terekhova, I.V. and Kulikov, O.V., Russ. Chem. Bull., 1999, no. 12, p. 2259.

    Google Scholar 

  20. Terekhova, I.V., Lapshev, P.V., and Kulikov, O.V., Russ. J. Phys. Chem., A, 2000, vol. 74, no. 11, p. 1830.

    Google Scholar 

  21. Terekhova, I.V., Kumeev, R.S., and Alper, G.A., J. Incl. Phenom. Macrocyclic Chem., 2008, vol. 62, p. 363.

    Article  CAS  Google Scholar 

  22. Zielenkiewics, W., Terekhova, I.V., Koźbial, M., and Kumeev, R.S., J. Therm. Anal. Calorim., 2010, vol. 101, p. 595.

    Article  Google Scholar 

  23. Terekhova, I.V., Tikhova, M.N., Volkova, T.V., Kumeev, R.S., Perlovich, G.L., J. Incl. Phenom. Macrocycl. Chem., 2011, vol. 69, p. 167.

    Article  CAS  Google Scholar 

  24. Terekhova, I.V., Lapshev, P.V., and Kulikov, O.V., Russ. J. Coord. Chem., 2003, vol. 29, no. 1, p. 73.

    Article  CAS  Google Scholar 

  25. Buschmann, H.-J., Mutihac, L., and Jansen, K., J. Incl. Phenom. Macrocyclic Chem., 2001, vol. 39, p. 1.

    Article  CAS  Google Scholar 

  26. Buschmann, H.-J. and Mutihac, L., J. Incl. Phenom. Macrocyclic Chem., 2002, vol. 42, p. 193.

    Article  CAS  Google Scholar 

  27. Mutihac, L., Buschmann, H.-J., Jansen, K., and Wego, A., Mater. Sci. Eng. (C), 2001, vol. 18, p. 259.

    Article  Google Scholar 

  28. Buschmann, H.J., Schollmeyer, E., and Mutihac, L., Thermochim. Acta, 1998, vol. 316, p. 189.

    Article  CAS  Google Scholar 

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

    CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  31. Danil de Namor, A.F., Traboulssi, R., and Lewis, D.F.V., J. Am. Chem. Soc., 1990, vol. 112, no. 23, p. 8442.

    Article  CAS  Google Scholar 

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

    Google Scholar 

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

    Article  CAS  Google Scholar 

  34. Dostizheniya i problemy teorii sol’vatatsii: strukturno-termodinamicheskie aspekty (Achievements and Problems of the Theory of Solvation: Structural and Thermodynamic Aspects), Moscow: Nauka, 1998, p. 172.

  35. Sharnin, V.A., Zh. Obshch. Khim., 1994, vol. 64, no. 11, p. 1914.

    Google Scholar 

  36. Sharnin, V.A., Russ. J. Coord. Chem., 1996, vol. 22, no. 5, p. 394.

    Google Scholar 

  37. Sharnin, V.A., Izv. Vuzov, Ser. Khim. i Khim. Tekhnol., 2005, vol. 48, no. 7, p. 44.

    CAS  Google Scholar 

  38. Sharnin, V.A., Russ. J. Gen. Chem., 1999, vol. 69, no. 9, p. 1368.

    CAS  Google Scholar 

  39. Sharnin, V.A., Russ. J. Gen. Chem., 2001, vol. 71, no. 9, p. 1373.

    Article  CAS  Google Scholar 

  40. Usacheva, T.R., Ledenkov, S.F., and Sharnin, V.A., J. Therm. Anal. Calorim., 2002, vol. 70., P., 209.

    Article  CAS  Google Scholar 

  41. Usacheva, T.R., Ledenkov, S.F., and Sharnin, V.A., J. Therm. Anal. Calorim, vol. 70, 2002, p. 379.

    Article  CAS  Google Scholar 

  42. Wada, G., Tamura, E., Okina, M., and Nakamura, M., Bull. Chem. Soc. Jpn., 1982, vol. 55, no. 10, p. 3064.

    Article  CAS  Google Scholar 

  43. Kulikov, O.V., Krestov, G.A., and Zielenkiewicz, W., J. Solut. Chem., 1995, vol. 24, no. 11, p. 1155.

    Article  CAS  Google Scholar 

  44. Kulikov, O.V. and Krestov, G.A., Pure Appl. Chem., 1995, vol. 67, no. 7, p. 1103.

    CAS  Google Scholar 

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

    Article  Google Scholar 

  46. Hamman, S., Salon, M.C., and Bjguin, C., Org. Magn. Res., 1982, vol. 20, no. 2, p. 78.

    Article  CAS  Google Scholar 

  47. Matteoli, E., Lepori, L., Usacheva, T.R., and Sharnin, V.A., J. Therm. Anal. Calorim., 2009, vol. 97, no. 3, p. 811.

    Article  CAS  Google Scholar 

  48. Usacheva, T.R., Sharnin, V.A., and Matteoli, E., Russ. J. Phys. Chem., A, 2011, vol. 85, no. 11, p. 1898.

    Article  CAS  Google Scholar 

  49. Usacheva, T.R., Sharnin, V.A., Chernov, I.V., and Matteoli, E., J. Therm. Anal. Calorim., 2013, vol. 112, p. 983.

    Article  CAS  Google Scholar 

  50. Usacheva, T.R., Kuz’mina, I.A., Sharnin, V.A., Chernov, I.V., and Matteoli, E., Russ. J. Phys. Chem., A, 2012, vol. 86, no. 1, p. 36.

    Article  CAS  Google Scholar 

  51. Usacheva, T.R., Kuz’mina, I.A., Sharnin, V.A., Chernov, I.V., and Matteoli, E., Russ. J. Phys. Chem., A, 2012, vol. 86, no. 7, p. 1064.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  53. Borodin, V.A., Kozlovskij, E.V., and Vasil’ev, V.P., Zh. Neorg. Khim., 1982, vol. 27, no. 9, p. 2169.

    CAS  Google Scholar 

  54. Usacheva, T.R., Kuz’mina, I.A., Dzhumasheva, M.O., Sidorenko, N.S., and Sharnin, V.A., Izv. Vuzov, Ser. Khim. i Khim. Tekhnol., 2010, vol. 53, no. 12, p. 51.

    CAS  Google Scholar 

  55. Usacheva, T.R., Kuz’mina, I.A., Sharnin, V.A., Sidorenko, N.S., and Voronina, S.I., Russ. J. Phys. Chem., A, 2011, vol. 85, no. 6, p. 948.

    Article  CAS  Google Scholar 

  56. Dey, B.P. and Lahiri, S.C., Indian J. Chem., 1986, vol. 25A, p. 136.

    CAS  Google Scholar 

  57. Gesse, Zh.F., Isaeva, V.A., and Sharnin, V.A., Russ. J. Phys. Chem., A, 2010, vol. 84, no. 2, p. 329.

    Article  CAS  Google Scholar 

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Correspondence to T. R. Usacheva.

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Original Russian Text © T.R. Usacheva, V.A. Sharnin, 2014, published in Zhurnal Obshchei Khimii, 2014, Vol. 84, No. 2, pp. 234–241.

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Usacheva, T.R., Sharnin, V.A. Formation of molecular complexes between 18-crown-6 and amino acids in aqueous-organic media. Russ J Gen Chem 84, 227–234 (2014). https://doi.org/10.1134/S1070363214020121

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