Central European Journal of Chemistry

, Volume 11, Issue 5, pp 655–663

Aromatic properties of 8-hydroxyquinoline and its metal complexes

  • Krzysztof K. Zborowski
  • Miquel Solá
  • Jordi Poater
  • Leonard M. Proniewicz
Invited Paper

DOI: 10.2478/s11532-013-0215-6

Cite this article as:
Zborowski, K.K., Solá, M., Poater, J. et al. cent.eur.j.chem. (2013) 11: 655. doi:10.2478/s11532-013-0215-6

Abstract

Chelatoaromaticity (aromaticity of chelate complexes) has been recently recognized as an important property influencing the stability of chelate compounds. In this paper, aromaticity of various forms of 8-hydroxyquinoline (anion, neutral molecule, zwitterion and cation) as well as its chelate complexes with magnesium and aluminium ions are investigated. Aromatic properties of these compounds are analyzed using several aromaticity indices based on energetic, geometric, magnetic and electronic physical manifestations of this phenomenon. Results of performed calculations have shown different aromatic properties for the two rings (pyridine and benzene) occurring in the studied ligand. Aromaticity of these rings in metal complexes of 8-hydroxyquinoline is significantly higher than that in corresponding ligand anion. This means that during complexation the aromaticity of the ligand increases and the chelatoaromatic effect stabilizes the studied metal complexes. In contrast, metallocyclic rings of studied metal complexes have non-aromatic properties, and, consequently, the metallocyclic ring is not stabilized by chelatoaromaticity. We conclude that, in the complex, every 8-hydroxyquinoline unit and the metal ion are separated p-electronic systems.
https://static-content.springer.com/image/art%3A10.2478%2Fs11532-013-0215-6/MediaObjects/11532_2013_215_Fig1_HTML.jpg

Keywords

8-hydroxyquinolineAromaticityChelatocomplexesChelatoaromaticity

Copyright information

© Versita Warsaw and Springer-Verlag Wien 2013

Authors and Affiliations

  • Krzysztof K. Zborowski
    • 1
  • Miquel Solá
    • 2
  • Jordi Poater
    • 2
  • Leonard M. Proniewicz
    • 1
    • 3
  1. 1.Faculty of ChemistryJagiellonian UniversityKrakówPoland
  2. 2.Institute of Computational Chemistry and Department of ChemistryGirona UniversityGirona, CataloniaSpain
  3. 3.The State Higher Vocational SchoolTarnówPoland