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Paper | Regular issue | Vol 78, No. 2, 2009, pp.425-433
Published online, 6th October, 2008
DOI: 10.3987/COM-08-11523
■ NMR Studies of 2-Aryl Derivatives of Benzimidazole, Benzimidazolium Ion, and Benzimidazoline

Chang Kiu Lee and In-Sook Han Lee*

*Department of Chemistry, Kangwon National University, Chuncheon 200-701, S. Korea

Abstract

A series of 2-arylbenzimidazoles, 2-aryl-1,3-dimethylbenzimidazolium iodides, and 2-aryl-1,3-dimethylbenzimidazolines were prepared and their NMR spectra were examined. The substituent parameters were calculated for 2-benzimidazolyl, 2-benzimidazoliumyl, and 2-benzimidazolinyl groups on the chemical shifts of the protons and the carbons of benzene ring. The 2-benzimidazoliumyl group was found to cause a significant up-field shift of the ipso-carbon signal and down-field shift for the ortho- and para-carbon signals. On the other hand, the 2-benzimidazolyl and the 2-benzimidazolinyl groups cause down-field shift of the ipso-carbon signals but cause almost negligible change on the other carbon signals.