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Supramolecular chemistry of macrocyclic cavitand cucurbit[7]uril with isoleucine

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Abstract

The l-isoleucine — cucurbit[7]uril system in solution was studied at various concentrations by NMR spectroscopy. The 1H NMR spectra of the L-isoleucine complex with CB[7] in solution indicate an equilibrium between the unbound L-isoleucine species and L-isoleucine included in cucurbit[7]uril. The structural and thermodynamic parameters of inclusion compounds of cucurbituril with L-isoleucine 1—3, as well as of supramolecular adduct 4 formed due to hydrogen bonding between the amino acid and the macrocycle, were calculated using the density functional theory (DFT) with the PBE functional. The protonated L-isoleucine in the structures of inclusion complexes 1—3 is completely or partially accommodated in the interior of the cavity of the cavitand molecule, and in the supramolecular structure 4, it is outside the cavitand, which is energetically most favorable.

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Authors and Affiliations

  1. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, 3 prosp. Akad. Lavrentieva, 630090, Novosibirsk, Russian Federation

    E. A. Kovalenko & D. A. Maynichev

  2. Kazan National Research Technological University, 68 ul. K. Marksa, 420015, Kazan, Russian Federation

    A. N. Masliy & A. M. Kuznetsov

Authors
  1. E. A. Kovalenko
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  2. D. A. Maynichev
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  3. A. N. Masliy
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  4. A. M. Kuznetsov
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Corresponding author

Correspondence to E. A. Kovalenko.

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

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1906—1911, August, 2015.

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Kovalenko, E.A., Maynichev, D.A., Masliy, A.N. et al. Supramolecular chemistry of macrocyclic cavitand cucurbit[7]uril with isoleucine. Russ Chem Bull 64, 1906–1911 (2015). https://doi.org/10.1007/s11172-015-1092-2

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  • DOI: https://doi.org/10.1007/s11172-015-1092-2

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