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Russian Journal of Organic Chemistry

, Volume 49, Issue 9, pp 1386–1396 | Cite as

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

  • 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
Article
  • 107 Downloads

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.

Keywords

Benzene Ring Crown Ether Guest Molecule Carboxy Group Ammonium Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • N. E. Kuz’mina
    • 1
  • V. A. Yashkir
    • 1
  • S. V. Moiseev
    • 1
  • O. V. Fedorov
    • 2
  • E. V. Rakhmanov
    • 2
  • N. S. Baleeva
    • 2
  • A. V. Tarakanova
    • 2
  • A. V. Anisimov
    • 2
  1. 1.Scientific Center for Appraisal of Medical FacilitiesMinistry of Health Protection of RussiaMoscowRussia
  2. 2.Faculty of ChemistryMoscow State UniversityMoscowRussia

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