Abstract
The parameters of the acid-base and tautomeric equilibria of the E (syn) isomers of 1-methyl-substituted benzimidazole-2-carbaldehyde oxime, imidazole-2-carbaldehyde oxime, Δ2-imidazoline-2-carbaldehyde oxime, and Δ2-pyrazoline-3-carbaldehyde oxime in aqueous solutions at 25°C have been determined by a potentiometric method using model compounds. The tautomeric ratio (zwitterion)/(uncharged form) rises in parallel with an increase in the basicity of the parent heterocycle. Unlike known heterocyclic aldoximes, 1-methyl-Δ2-imidazoline-2-carboxaldehyde oxime exists in the zwitterionic form.
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