Boron coordination compounds derived from 2-phenyl-benzimidazole and 2-phenyl-benzotriazole bidentate ligands |
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Authors: | Adriana Esparza-Ruiz Heinrich Nöth Rosalinda Contreras |
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Institution: | a Department of Chemistry, Cinvestav, AP 14-740, CP 07000, México DF, Mexico b Department Chemie, Ludwig-Maximiliams Universität, Butenandt-Strasse 5-13 (Haus D), D-81377 Munich, Germany |
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Abstract: | The syntheses and structural analyses of a series of boron heterocycles derived from 2-(1H-benzimidazol-2-yl)-phenylamine (1), 2-(1H-benzimidazol-2-yl)-phenol (2), 2-(1H-benzimidazol-2-yl)-benzenedisulfide (3), 2-3-(1,1,1,3,-tetramethyl-butyl)-phenyl]-2H-benzotriazole (4), 2-3,5-bis-(1-methyl-1-phenylethyl)-phenyl]-2H-benzotriazole (5) and (C6H5)2BOH or BF3·OEt2 are reported. The new boron compounds: diphenyl-2-(1H-benzimidazol-2-yl-κN)-phenylamide-κN]-boron (6), diphenyl-2-(1H-benzimidazol-2-yl-κN)-phenolate-κO]-boron (7), diphenyl-2-(1H-benzimidazol-2-yl-κN)-benzenethiolate-κS]-boron (8), diphenyl-2-(2H-benzotriazol-2-yl-κN)-4-(1,1,3,3-tetramethyl-butyl)-phenolate-κO]-boron (9), diphenyl-2-(2H-benzotriazol-2-yl-κN)-4,6-(1-methyl-1-phenylethyl)-phenolate-κO]-boron (10), difluoro-2-(1H-benzimidazol-2-yl-κN)-phenolate-κO]-boron (11), difluoro-2-(2H-benzotriazol-2-yl-κN)-4-(1,1,3,3-tetramethylbutyl)-phenolate-κO]-boron (12) and difluoro-2-(2H-benzotriazol-2-yl-κN)-4,6-(1-methyl-1-phenylethyl)-phenolate-κO]-boron (13) have four fused rings, with boron included in a six-membered ring and bound to N, O or S atoms and strongly coordinated by a nitrogen atom from the imidazole or triazole rings. Their structures are zwitterionic, with a negative charge on the boron and a delocalized positive charge on the ligand. Compounds 6-12 were studied by NMR, IR, mass spectrometry, and 6-10 and 12 by X-ray diffraction analyses. |
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Keywords: | Organoboron 2-Phenyl-benzimidazole 2-Phenyl-benzotriazole Coordination compounds 11B and 19F NMR |
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