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dc.contributor.authorHolschbach, Marcus H.-
dc.contributor.authorSanz, Dionisia-
dc.contributor.authorClaramunt, Rosa M.-
dc.contributor.authorInfantes, L.-
dc.contributor.authorMotherwell, Sam-
dc.contributor.authorRaithby, Paul R.-
dc.contributor.authorJimeno, M. Luisa-
dc.contributor.authorHerrero, David-
dc.contributor.authorAlkorta, Ibon-
dc.contributor.authorJagerovic, Nadine-
dc.contributor.authorElguero, José-
dc.identifier.citationJournal of Organic Chemistry 68 : 8831-8837 (2003)es_ES
dc.description.abstractThe 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 NHâââOdN hydrogen bonds: one is intramolecular, the other links adjacent molecules in an infinite chain.es_ES
dc.description.sponsorshipout with use of direct methods SIR97,19 and the least-squares refinement was performed in SHELXL9720 with F2 magni-tudes. Computational Details. The optimization of the structures of all compounds discussed in this paper was carried out at the B3LYP/6-311++G** level,21,22 using the facilities of the Gaussian 98 set of programs.23 Absolute shielding were calculated, at the same level, over these geometries within the GIAO approximation.24,25 Acknowledgment. Financial support was provided by the Spanish DGICYT (Project Nos. BQU-2000-0252 and BQU-2000-0906). Dr. Roberto Sastre (CSIC, Madrid) helped us with the electronic spectra at low tempera-tures. L.I. acknowledges the “Ministerio de Educacion y Cultura” of Spain for a postdoctoral fellowship. Supporting Information Available: Crystallographic information for 2a (CIF file)and computational results (total energy and geometry) optimized at the B3LYP/6-311++G** level. This material is available free of charge via the Internet at JO034833U (23) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.;es_ES
dc.publisherAmerican Chemical Societyes_ES
dc.titleStructure of a 4-nitroso-5-aminopyrazole and its salts: Tautomerism, protonation, and E/Z isomerismes_ES
dc.description.peerreviewedPeer reviewedes_ES
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