2,2-Dialkyl-2H-benzimidazoles, the high energy tautomers of the corresponding 1,2-dialkyl-1H-benzimidazoles. Syntheses and their complexes with Cu(I) and Ag(I)

Goutam K. Patra, Israel Goldberg, Michael G.B. Drew, Senjuti De, Jnan P. Naskar, Dipankar Datta

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Abstract

Reaction of Cu(1,2-phenylenediamine)2(ClO4) 2 with neat RR'=O (R = methyl and/or ethyl) gives Cu(2,2-dialkyl-2H-benzimidazole)ClO4, demetallation of which by the action of aqueous ammonia yields pure 2,2-dialkyl-2H-benzimidazoles. These are characterised by NMR. In the X-ray crystal structure, Ag(2,2-methyl-2H-benzimi- dazole)NO3 is found to be a spiral ID coordination polymer where the 2H-benzimidazole acts as an N,N bridge between two Ag(I) centers. Although 2H-benzimidazoles are very unstable in the free stale, they are quite stable in their Cu(I) and Ag(I) complexes. The 1,2-tautomerisation in imidazole and benzimidazole have been studied by means of transition state calculations at B3LYP/6-3H+G(2d,p)* level.

Original languageEnglish
Pages (from-to)1758-1762
Number of pages5
JournalIndian Journal of Chemistry - Section A Inorganic, Physical, Theoretical and Analytical Chemistry
Volume46
Issue number11
StatePublished - Nov 2007

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