Amb motiu del tancament d'estiu, la validació de documents es reprendrà a partir del 28 d'agost de 2026. Disculpeu les molèsties.
Con motivo del cierre de verano, la validación de documentos se reanudará a partir del 28 de agosto de 2026. Disculpad las molestias
Due to the summer closure, document validation will resume starting August 28, 2026. We apologize for any inconvenience.

Fitxers

691780.pdf (1.95 MB)

Tipus de document

Article

Versió

Versió acceptada

Data de publicació

2019-06-22

Tots els drets reservats

Si us plau utilitzeu sempre aquest identificador per citar o enllaçar aquest document: https://hdl.handle.net/2445/162559

Gallic Acid Dimer As a Double π−Hole Donor: Evidence from X‑ray, Theoretical Calculations, and Generalization from the Cambridge Structural Database

Títol de la revista

Autors

Director/Tutor

ISSN de la revista

Títol del volum

Recurs relacionat

https://doi.org/10.1021/acs.cgd.9b00387

Resum

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.

Matèries

Química supramolecular, Èters, Hidrocarburs

Matèries (anglès)

Supramolecular chemistry, Ethers, Hydrocarbons

Citació

Col·leccions

Articles publicats en revistes (Mineralogia, Petrologia i Geologia Aplicada)

Citació

PROHENS LÓPEZ, Rafael, et al. 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, num. 7, pags. 3989-3997. ISSN 1528-7483. [consulted: 19 of August of 2026]. Available at: https://hdl.handle.net/2445/162559

Exportar metadades

JSON - METS

Compartir registre