Prohens López, Rafaelde-Sande, DafneFont Bardia, Ma. MercedesFranconetti, AntonioGonzález, J. F.Frontera, Antonio2020-05-272020-06-222019-06-221528-7483https://hdl.handle.net/2445/162559In 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.29 p.application/pdfeng(c) American Chemical Society , 2019Química supramolecularÈtersHidrocarbursSupramolecular chemistryEthersHydrocarbonsinfo:eu-repo/semantics/article6917802020-05-27info:eu-repo/semantics/openAccess