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Magnetic response and its relation to the keto-enol tautomerism of 3,3′-(1,4-phenylene)bis(pentane-2,4-dione): Experimental and theoretical insights |
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| Authors: | Andres Lancheros Ximena Zarate Eduardo Schott |
| Institution: | 1. Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Santiago, Chile
Millenium Nuclei on Catalytic Processes Towards Sustainable Chemistry (CSC), Santiago, Chile Contribution: Formal analysis, Methodology, Writing - original draft, Writing - review & editing;2. Instituto de Ciencias Químicas Aplicadas, Theoretical and Computational Chemistry Center, Facultad de Ingeniería, Universidad Autónoma de Chile, Santiago, Chile;3. Facultad de Química y de Farmacia, Pontificia Universidad Católica de Chile, Santiago, Chile |
| Abstract: | A direct correlation between aromaticity and the thermodynamic stability in the tautomeric equilibrium of 3,3′-(1,4-phenylene)bis(pentane-2,4-dione) is studied using experimental methods and theoretical approaches. According to the results, the most abundant tautomer corresponds to the bis-β-keto-enol tautomer when conditions such as temperature, solvent polarity, and pH are deliberately changed. Theoretical results of aromaticity analysis showed good concordance with the experimental results, using rigorous computations such as induced magnetic field (Bind) and free of in-plane component NICS (FIPC-NICS). |
| Keywords: | aromaticity induced magnetic fields tautomerism |