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Crystal structure and UV spectra of a 1,2-disubstituted benzimidazolium chloride
1-(2-Hydroxybenzyl)-2-(2-hydroxyphenyl)-1H-benzimidazol-3-ium chloride, C(20)H(17)N(2)O(2) (+)·Cl(−), 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 th...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5598836/ https://www.ncbi.nlm.nih.gov/pubmed/28932424 http://dx.doi.org/10.1107/S205698901700977X |
Sumario: | 1-(2-Hydroxybenzyl)-2-(2-hydroxyphenyl)-1H-benzimidazol-3-ium chloride, C(20)H(17)N(2)O(2) (+)·Cl(−), 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—H⋯Cl and N—H⋯Cl 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 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. |
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