Article Dans Une Revue Crystal Growth & Design Année : 2021

An unusual intermolecular interaction between a lone pair and an electron-rich π-electron system of a quinoid dianion

Résumé

The crystal structure of lithium 2,5-dihydroxyquinonate dihydrate bis(dimethylsulfoxide) solvate [Li2DHQ(H2O)2(DMSO)2] reveals a close contact between the lone pair on the electropositive S atom of DMSO and the dianionic quinoid ring. This contact, resembling a π-hole interaction involving a dianion as an acceptor was studied in detail by a combination of X-ray charge density and quantum chemical modelling. Topology of electron density reveals a bond path and a (3,-1) critical point between the S atom of the DMSO and a C atom of the quinoid ring, while analysis of electrostatic potential indicates that the interaction between these two atoms is repulsive. However, the global electrostatic interaction between the DMSO and the dihydroxyquinonate moieties is attractive (-19.1 kJ/mol), as well as total in vacuo interaction energy (-42.8 kJ/mol).

Fichier principal
Vignette du fichier
2021_HAL_Vukovic_DMSO.pdf (2.41 Mo) Télécharger le fichier
Origine Fichiers produits par l'(les) auteur(s)
Licence

Dates et versions

hal-03474680 , version 1 (10-12-2021)
hal-03474680 , version 2 (31-01-2022)

Licence

Identifiants

Citer

Vedran Vuković, Tomislav Piteša, Christian Jelsch, Emmanuel Wenger, Krešimir Molčanov. An unusual intermolecular interaction between a lone pair and an electron-rich π-electron system of a quinoid dianion. Crystal Growth & Design, 2021, 21 (10), pp.5651-5658. ⟨10.1021/acs.cgd.1c00492⟩. ⟨hal-03474680v2⟩
82 Consultations
238 Téléchargements

Altmetric

Partager

  • More