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Complex formation of crown ethers with α-amino acids: Estimation by NMR spectroscopy

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Abstract

Complex formation of 18-crown-6 and dibenzo crowns with glycine, leucine, and norleucine was studied by NMR spectroscopy. The efficiency of non-valence interactions with participation of different active centers of the host and guest molecules is determined by solvation effects, mutual arrangement of benzene rings in dibenzo crowns, and the presence of bulky aliphatic substituents in the α-amino acid. The complexation of dibenzo crowns with α-amino acids in acid medium involves a system of different non-valence interactions, the most efficient of which are NH +3 ... O hydrogen bond between the ammonium group in the guest molecule and ether oxygen atoms in the host molecule and dipole-dipole interaction between the guest ammonium group and host benzene ring (NH +3 ... Ar). The efficiency of NH +3 ... O hydrogen bonding decreases in going from 18-crown-6 to dibenzo crowns due to distortion of symmetry of the macroring cavity and violation of geometric complementarity of some ether oxygen atoms. The integral efficiency of non-valence interactions in the system dibenzo crown-α-amino acid was estimated on a quantitative level by 1H NMR relaxation technique.

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References

  1. Steed, J.W. and Atwood, J.L., Supramolecular Chemistry, Chichester: Wiley, 2000. Translated under the title Supramolekulyarnaya khimiya, Moscow: Akademkniga, 2007, vols. 1, 2.

    Google Scholar 

  2. Terekhova, I.V., Kulikov, O.V., and Barannikov, V.P., Russ. J. Gen. Chem., 2004, vol. 74, p. 1213.

    Article  CAS  Google Scholar 

  3. Kulikov, O.V. and Kornilova, N.Yu., Zh. Fiz. Khim., 1996, vol. 70, p. 2119.

    CAS  Google Scholar 

  4. Kitaigorodskii, A.I., Molekulyarnye kristally (Molecular Crystals), Moscow: Nauka, 1971, p. 15.

    Google Scholar 

  5. Günther, H., NMR Spectroscopy: An Introduction, Chichester: Wiley, 1980. Translated under the title Vvedenie v kurs spektroskopii YaMR, Moscow: Mir, 1984, p. 104.

    Google Scholar 

  6. Derome, A.E., Modern NMR Techniques for Chemistry Research, Oxford: Pergamon, 1987.

    Google Scholar 

  7. Sass, M. and Ziesson, D., J. Magn. Reson., 1977, vol. 25, p. 263.

    CAS  Google Scholar 

  8. Lambert, J.B. and Mazzola, E.P., Nuclear Magnetic Resonance Spectroscopy. An Introduction to Principles, Applications, and Experimental Methods, Upper Saddle River, NJ: Pearson/Prentice Hall, 2004, p. 317.

    Google Scholar 

  9. Bakhmutov, V.I., Practical NMR Relaxation for Chemists, Chichester: Wiley, 2004, p. 64.

    Book  Google Scholar 

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Authors and Affiliations

  1. Scientific Center for Appraisal of Medical Facilities, Ministry of Health Protection of Russia, Moscow, Russia

    N. E. Kuz’mina, V. A. Yashkir & S. V. Moiseev

  2. Faculty of Chemistry, Moscow State University, Leninskie gory 1, Moscow, 119991, Russia

    O. V. Fedorov, E. V. Rakhmanov, N. S. Baleeva, A. V. Tarakanova & A. V. Anisimov

Authors
  1. N. E. Kuz’mina
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  2. V. A. Yashkir
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  3. S. V. Moiseev
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  4. O. V. Fedorov
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  5. E. V. Rakhmanov
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  6. N. S. Baleeva
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  7. A. V. Tarakanova
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  8. A. V. Anisimov
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Corresponding author

Correspondence to A. V. Anisimov.

Additional information

Original Russian Text © N.E. Kuz’mina, V.A. Yashkir, S.V. Moiseev, O.V. Fedorov, E.V. Rakhmanov, N.S. Baleeva, A.V. Tarakanova, A.V. Anisimov, 2013, published in Zhurnal Organicheskoi Khimii, 2013, Vol. 49, No. 9, pp. 1401–1412.

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Kuz’mina, N.E., Yashkir, V.A., Moiseev, S.V. et al. Complex formation of crown ethers with α-amino acids: Estimation by NMR spectroscopy. Russ J Org Chem 49, 1386–1396 (2013). https://doi.org/10.1134/S1070428013090261

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  • DOI: https://doi.org/10.1134/S1070428013090261

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