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

M H Holschbach, D Sanz, R M Claramunt, L Infantes, S Motherwell, P R Raithby, M L Jimeno, D Herrero, L Alkorta, N Jagerovic, J Elguero

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21 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)8831-8837
Number of pages7
JournalJournal of Organic Chemistry
Volume68
Issue number23
DOIs
Publication statusPublished - 2003

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