1-(2-Hydroxybenzyl)-2-(2-hydroxyphenyl)-1H-benzimidazol-3-ium chloride, C 20 H 17 N 2 O 2 + ÁCl À , was prepared by reaction of salicylaldehyde with o-phenylenediamine in the presence of trimethylsilyl chloride acting as a source of HCl. As a result of steric hindrance, the cation in the crystal is far from planar: the benzimidazole ring system makes dihedral angles of 55.49 (9) and 81.36 (8) with the planes of the phenolic groups. The crystal packing is dominated by O-HÁ Á ÁCl and N-HÁ Á ÁCl hydrogen bonds, which link the cations and anions into four-membered rings and then into chains along [100]. The title compound exhibits two transitions in the UV region, which are revealed in the solid state and solution spectra as an absorption maximum at 280 nm and a shoulder at 320 nm. According to the results of TD-DFT calculation, both transitions have a -* nature and the molecular orbitals involved in these transitions are mostly localized on the benzimidazole ring system and on the phenyl ring attached to it at the 2-position.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.