Structure of a 4-nitroso-5-aminopyrazole and its salts: tautomerism, protonation, and E/Z isomerism |
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Authors: | Holschbach Marcus H Sanz Dionisia Claramunt Rosa M Infantes Lourdes Motherwell Sam Raithby Paul R Jimeno María Luisa Herrero David Alkorta Ibon Jagerovic Nadine Elguero José |
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Institution: | Institut für Nuklearchemie (INC), Forschungszentrum Juelich, D-52425 Juelich, Germany. m.holschbach@fz-juelich.de |
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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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