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Benzimidazole or diamide from a reaction of diamines and carboxylic acids or acid chlorides: crystal structures and theoretical studies

Felix Odame, Eric Hosten, Richard Betz, Kevin Lobb, Zenixole Tshentu


A reaction of an acid chloride with a diamine yielded a diamide. m-Toluic acid was chlorinated to m-toluoyl chloride and subsequently reacted with 4-methyl-o-phenylenediamine in pyridine to obtain 3-methyl-N-[2-(3-methylbenzamido)phenylbenzamide (I). 2-(3-Methylphenyl)-1H-benzimidazole (II) has been obtained upon reacting o-phenylenediamine with m-toluic acid in polyphosphoric acid and toluene. The compounds have been characterized by IR, NMR, microanalyses and GC−MS. The crystal structures of the compounds have been discussed. DFT calculations of the frontier orbitals of the precursor compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity in the formation of the diamides and benzimidazoles. The synthesis of the amide from a diamine was seen to be favoured in the presence of a good leaving group attached to the carbonyl as in the case of acid chloride. However, the synthesis of benzimidazoles was found to be favoured in the presence of an excess of a protonating agent and high temperature


m-toluic acid; diamine; diamide; benzimidazoles; crystal structures; frontier orbitals

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Copyright (c) 2015 Felix Odame, Eric Hosten, Richard Betz, Kevin Lobb, Zenixole Tshentu

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