Theoretical studies on aromaticity of selected hydroxypyrones. Part 3#. Chelatoaromaticity phenomenon in metalcomplexes of hydroxypyrones |
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| Authors: | Krzysztof K. Zborowski Miquel Solà Jordi Poater Leonard M. Proniewicz |
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| Affiliation: | 1. Faculty of Chemistry, Jagiellonian University, 3 Ingardena Street, 30‐060 Kraków, Poland;2. Institut de Química Computacional and Departament de Química, Universitat de Girona, Campus de Montilivi, 17071 Girona, Catalonia, Spain;3. Regional Laboratory of Physicochemical Analyses and Structural Research, Jagiellonian University, 3 Ingardena Street, 30‐060 Kraków, Poland |
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| Abstract: | The aim of this project is to study the aromatic properties of various forms (neutral, cationic, and anionic) of selected hydroxypyrones (pyromeconic acid, maltol, and ethylmaltol) and their metalcomplexes with aluminum, gallium, and indium ions. Aromaticity of hydroxypyrone metalcomplexes is important because it can influence the stability of such complexes, which is crucial for their applications in medicinal and environmental chemistry. Results from ten different indices of aromaticity (HOMA, NICS(0), NICS(1), NICSscan, ASEiso, PDI, FLU, Iring, MCI, and KMCI) show that aromaticity in hydroxypyrones decreases in the order cations > neutral molecules > anions. Performed calculations situate the aromaticities of ligands in metalcomplexes close to their respective cations. This means that complexation causes a significant increase of the aromaticity of ligands, which stabilizes formed chelatocomplexes. On the other hand, we clearly show that rings that are involved in binding metal ions are not aromatic. Copyright © 2010 John Wiley & Sons, Ltd. |
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| Keywords: | aromaticity chelatocomplexes density functional theory hydroxypyrones metalloaromaticity |
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