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Aromatic properties of 8-hydroxyquinoline and its metal complexes

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

Authors kindly acknowledge Warsaw University’s Interdiciplinary Centre for Mathematical and Computational Modelling, "ICM" (project number G17-8). This research was financed by the Polish Ministry of Science and Higher Education (grant no. N N204 544839). Moreover, the following organizations are thanked for financial support: the Ministerio de Ciencia e Innovacion (MICINN, project numbers CTQ2011-23156/BQU and CTQ2011-25086/BQU), the Generalitat de Catalunya (project number 2009SGR637 and Xarxa de Referencia en Quimica Teorica i Computacional), and the FEDER fund (European Fund for Regional Development) for the grant UNGI08-4E-003. Excellent service by the Centre de Serveis Cientifics i Academics de Catalunya (CESCA) is gratefully acknowledged

© Central European Journal of Chemistry, 2013, vol. 11, núm. 5, p. 655-663

Springer Verlag

Autor: Zborowski, Krzysztof K.
Solà i Puig, Miquel
Poater i Teixidor, Jordi
Proniewicz, Leonard M.
Data: 1 maig 2013
Resum: 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
Authors kindly acknowledge Warsaw University’s Interdiciplinary Centre for Mathematical and Computational Modelling, "ICM" (project number G17-8). This research was financed by the Polish Ministry of Science and Higher Education (grant no. N N204 544839). Moreover, the following organizations are thanked for financial support: the Ministerio de Ciencia e Innovacion (MICINN, project numbers CTQ2011-23156/BQU and CTQ2011-25086/BQU), the Generalitat de Catalunya (project number 2009SGR637 and Xarxa de Referencia en Quimica Teorica i Computacional), and the FEDER fund (European Fund for Regional Development) for the grant UNGI08-4E-003. Excellent service by the Centre de Serveis Cientifics i Academics de Catalunya (CESCA) is gratefully acknowledged
Format: application/pdf
ISSN: 1895-1066 (versió paper)
1644-3624 (versió electrònica)
Accés al document: http://hdl.handle.net/10256/11393
Llenguatge: eng
Editor: Springer Verlag
Col·lecció: MICINN/PN 2012-2014/CTQ2011-23156
MICINN/PN 2012-2014/CTQ2011-25086
AGAUR/2009-2014/2009 SGR-637
Reproducció digital del document publicat a: http://dx.doi.org/10.2478/s11532-013-0215-6
Articles publicats (D-Q)
És part de: © Central European Journal of Chemistry, 2013, vol. 11, núm. 5, p. 655-663
Drets: Tots els drets reservats
Matèria: Aromaticitat (Química)
Aromaticity (Chemistry)
Quelats -- Propietats aomàtiques
Chelates -- Aromatic properties
Títol: Aromatic properties of 8-hydroxyquinoline and its metal complexes
Tipus: info:eu-repo/semantics/article
Repositori: DUGiDocs

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