Sigma-hole interactions in the molecular and crystal structures of N-boryl benzo-2, 1, 3-selenadiazoles. (1st June 2018)

• Record Type: Journal Article
• Authors: Lee, Jiwon; Lee, Lucia Myongwon; Arnott, Zachary; Jenkins, Hilary; Britten, James F.; Vargas-Baca, Ignacio
• Is Part Of: New journal of chemistry. Volume 42:Number 13(2018)
• Page Start: 10555
• Page End: 10562
• Publication Date: 2018-06-01
• Subjects: Chemistry -- Periodicals; Chimie -- Périodiques; 540
• DOI: 10.1039/c8nj00553b
• Languages: English
• ISSNs: 1144-0546

Abstract

Abstract : Crystallography and DFT reveal competition between chalcogen bonding and other intermolecular interactions. Abstract : N-Bonded adducts of benzo-2, 1, 3-selenadiazole with BX3 (X = Ph, F, Cl, Br) were prepared and crystallographically characterized. The structures of the 1 : 1 adducts of BF3 and BCl3 demonstrate dimerization through the [Se–N]2 supramolecular synthon and enhancement of the corresponding Se⋯N chalcogen bonding interactions. However, the structures of the BPh3 and BBr3 compounds indicate that other supramolecular interactions can efficiently compete and inhibit [Se–N]2 dimerization. In the case of the BPh3 adduct, dispersion favors a dimer featuring Se⋯C interactions. In the crystal of the BBr3 derivative, the cooperative effect of Se⋯N chalcogen bonding and Br⋯Br halogen bonding interactions lead to a network structure. A 1 : 2 adduct could be isolated only in the case of BCl3 ; its structure features short intramolecular Se⋯Cl interactions resulting from the enhanced electrophilic character of the chalcogen atom.