alexa Two tautomers in one crystal: 4(5)-nitro-5(4)-methoxyimidazole.


Organic Chemistry: Current Research

Author(s): Kubicki M

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Abstract The case of prototropic annular tautomerism in an imidazole derivative has been found. The crystal structure contains a 50:50 mixture of two tautomers: 4-nitro-5-methoxyimidazole and 5-nitro-4-methoxyimidazole. The X-ray experiment actually shows the superposition of these compounds; it appears as if the structure is centrosymmetric and the N-H hydrogen atoms are disordered over two ring N atoms. Owing to the hydrogen-bond pattern, the values of their site occupation factors have to be exactly equal to 1/2. The molecules are connected into a three-dimensional network by means of N-H...N and C-H...O hydrogen bonds. This article was published in Acta Crystallogr B and referenced in Organic Chemistry: Current Research

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