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Benzimidazoles. IV. Preparation, infrared, and ultraviolet absorption spectra of 1-methyl-2-aryl-5-nitrobenzimidazoles

A. Jurášek and R. Kada

Department of Organic Chemistry, Slovak Technical University, Bratislava

 

Abstract: By treatment of 4-nitro-2-amino-N-methylaniline with p-substituted benzaldehydes in nitrobenzene new 1-methyl-2-(4-X-phenyl)-5-nitrobenzimidazoles were prepared, where X = CH3, CI, Br, I, COOCH3. Infra-red absorption spectra of the described substances and those, where X = H, OCH3 and N(CH3)2 in the 1800—1200 cm-1 range are discussed and the electron absorption spectra in the near ultra-violet region are compared with those of isomeric 1-(4-X-phenyl)-2-methyl-5-nitrobenzimidazoles. It was found that the displacement of phenyl group from carbon C(1) to C(2) in 5-nitrobenzimidazoles resulted in formation of absorption bands corresponding to the benzenoid л→л* electron transition, whereas bands attributed to the electron transition in the imidazole ring remain „hidden".

Full paper in Portable Document Format: 224a257.pdf (in Slovak)

 

Chemical Papers 22 (4) 257–262 (1968)

Monday, February 26, 2024

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