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Gallic Acid Dimer As a Double π−Hole Donor: Evidence from X‑ray, Theoretical Calculations, and Generalization from the Cambridge Structural Database
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In this work, we demonstrate that the centrosymmetric eight-membered supramolecular ring R2 2 (8) that is formed upon dimerization of benzoic acids has a marked tendency to establish π−hole interactions with electron-rich atoms. We have used the Cambridge Structural Database to demonstrate the preference of carboxylic acid dimers to form donor−acceptor interactions involving π−holes located at the C atoms above and below the molecular plane. Moreover, we have carried out DFT calculations (PBE0-D3/def2-TZVP) to investigate the geometric and energetic features of these interactions and how they are affected by the substituents of the aromatic ring. Finally, as an example we report the synthesis and X-ray characterization of a solvate of gallic acid with dioxane, where two molecules of dioxane are located above and below the eight-membered supramolecular ring, forming two symmetrically equivalent O···C π−hole interactions.
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PROHENS LÓPEZ, Rafael, DE-SANDE, Dafne, FONT BARDIA, Ma. mercedes, FRANCONETTI, Antonio, GONZÁLEZ, J. f., FRONTERA, Antonio. Gallic Acid Dimer As a Double π−Hole Donor: Evidence from X‑ray, Theoretical Calculations, and Generalization from the Cambridge Structural Database. _Crystal Growth & Design_. 2019. Vol. 19, núm. 7, pàgs. 3989-3997. [consulta: 23 de gener de 2026]. ISSN: 1528-7483. [Disponible a: https://hdl.handle.net/2445/162559]