Invited Paper

Central European Journal of Chemistry

, Volume 11, Issue 5, pp 655-663

First online:

Aromatic properties of 8-hydroxyquinoline and its metal complexes

  • Krzysztof K. ZborowskiAffiliated withFaculty of Chemistry, Jagiellonian University Email author 
  • , Miquel SoláAffiliated withInstitute of Computational Chemistry and Department of Chemistry, Girona University
  • , Jordi PoaterAffiliated withInstitute of Computational Chemistry and Department of Chemistry, Girona University
  • , Leonard M. ProniewiczAffiliated withFaculty of Chemistry, Jagiellonian UniversityThe State Higher Vocational School

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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.


8-hydroxyquinoline Aromaticity Chelatocomplexes Chelatoaromaticity