Structure of a 4-nitroso-5-aminopyrazole and its salts: Tautomerism, protonation, and E/Z isomerism

Reference:

Holschbach, M. H., Sanz, D., Claramunt, R. M., Infantes, L., Motherwell, S., Raithby, P. R., Jimeno, M. L., Herrero, D., Alkorta, L., Jagerovic, N. and Elguero, J., 2003. Structure of a 4-nitroso-5-aminopyrazole and its salts: Tautomerism, protonation, and E/Z isomerism. Journal of Organic Chemistry, 68 (23), pp. 8831-8837.

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Abstract

The structures of 1-benzyl-4-nitroso-5-aminopyrazole (1) and its hydrochloride (1H(+)) have been determined in the solid state and in solution in DMSO, methanol, and ethanol. The free base exists in solution as a mixture of amino/nitroso tautomers 2a and 2b rather than in the imino/oxime tautomers 3. The conjugated cation 1H(+) results from the protonation of the nitroso group. X-ray crystallography showed that both amino hydrogen atoms of 2a form NH...O=N hydrogen bonds: one is intramolecular, the other links adjacent molecules in an infinite chain.

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