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1-(2-Hy­droxy­benz­yl)-2-(2-hy­droxy­phen­yl)-1 H -benzimidazol-3-ium chloride, C 20 H 17 N 2 O 2   + ·Cl − , is 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 the O—H⋯Cl and N—H⋯Cl hydrogen bonds. 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 π–π* 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.

Crystal structure and UV spectra of a 1,2-disubstituted benzimidazolium chloride