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dc.contributor.author
Romero, Angel H.  
dc.contributor.author
Fuentes, Germán  
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Suescun, Leopoldo  
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Piro, Oscar Enrique  
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Echeverría, Gustavo Alberto  
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Gotopo, Lourdes  
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Pezaroglo, Horacio  
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Álvarez, Guzmán  
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Cabrera, Gustavo  
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Cerecetto, Hugo  
dc.contributor.author
Couto, Marcos  
dc.date.available
2024-12-20T15:03:35Z  
dc.date.issued
2023-08  
dc.identifier.citation
Romero, Angel H.; Fuentes, Germán; Suescun, Leopoldo; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; et al.; Tautomerism and Rotamerism of Favipiravir and Halogenated Analogues in Solution and in the Solid State; American Chemical Society; Journal of Organic Chemistry; 88; 15; 8-2023; 10735-10752  
dc.identifier.issn
0022-3263  
dc.identifier.uri
http://hdl.handle.net/11336/250939  
dc.description.abstract
Favipiravir is an important selective antiviral against RNA-based viruses, and currently, it is being repurposed as a potential drug for the treatment of COVID-19. This type of chemical system presents different carboxamide-rotameric and hydroxyl-tautomeric states, which could be essential for interpreting its selective antiviral activity. Herein, the tautomeric 3-hydroxypyrazine/3-pyrazinone pair of favipiravir and its 6-substituted analogues, 6-Cl, 6-Br, 6-I, and 6-H, were fully investigated in solution and in the solid state through ultraviolet-visible, 1H nuclear magnetic resonance, infrared spectroscopy, and X-ray diffraction techniques. Also, a study of the gas phase was performed using density functional theory calculations. In general, the keto-enol balance in these 3-hydroxy-2-pyrazinecarboxamides is finely modulated by external and internal electrical variations via changes in solvent polarity or by replacement of substituents at position 6. The enol tautomer was prevalent in an apolar environment, whereas an increase in the level of the keto tautomer was favored by an increase in solvent polarity and, even moreso, with a strong hydrogen-donor solvent. Keto tautomerization was favored either in solution or in the solid state with a decrease in 6-substituent electronegativity as follows: H ≫ I ≈ Br > Cl ≥ F. Specific rotameric states based on carboxamide, “cisoide” and “transoide”, were identified for the enol and keto tautomer, respectively; their rotamerism is dependent on the tautomerism and not the aggregation state.  
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application/pdf  
dc.language.iso
eng  
dc.publisher
American Chemical Society  
dc.rights
info:eu-repo/semantics/openAccess  
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/  
dc.subject
Tautomerism and Rotamerism  
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Favipiravir and Halogenated 2 Analogues  
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X-ray diffraction  
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Física de los Materiales Condensados  
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Ciencias Físicas  
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CIENCIAS NATURALES Y EXACTAS  
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Físico-Química, Ciencia de los Polímeros, Electroquímica  
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Ciencias Químicas  
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CIENCIAS NATURALES Y EXACTAS  
dc.title
Tautomerism and Rotamerism of Favipiravir and Halogenated Analogues in Solution and in the Solid State  
dc.type
info:eu-repo/semantics/article  
dc.type
info:ar-repo/semantics/artículo  
dc.type
info:eu-repo/semantics/publishedVersion  
dc.date.updated
2024-11-25T14:01:42Z  
dc.journal.volume
88  
dc.journal.number
15  
dc.journal.pagination
10735-10752  
dc.journal.pais
Estados Unidos  
dc.description.fil
Fil: Romero, Angel H.. Universidad de la Republica; Uruguay  
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Fil: Fuentes, Germán. Universidad de la Republica; Uruguay  
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Fil: Suescun, Leopoldo. Universidad de la Republica; Uruguay  
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Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina  
dc.description.fil
Fil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina  
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Fil: Gotopo, Lourdes. Universidad Central de Venezuela. Facultad de Ciencias; Venezuela  
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Fil: Pezaroglo, Horacio. Universidad de la República; Uruguay  
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Fil: Álvarez, Guzmán. Universidad de la Republica; Uruguay  
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Fil: Cabrera, Gustavo. Universidad Central de Venezuela,.Facultad de Ciencias; Venezuela  
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Fil: Cerecetto, Hugo. Universidad de la Republica; Uruguay  
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Fil: Couto, Marcos. Universidad de la República; Uruguay  
dc.journal.title
Journal of Organic Chemistry  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1021/acs.joc.3c00777  
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.3c00777