Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study
- Autores
- Olivares, Fernando Gabriel; Lazcano, Francisco Gabriel; Castillo, Marcelo Omar; Barúa, María Gloria; Escalada, Juan Pablo; Pinto Vitorino, Graciela
- Año de publicación
- 2023
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- This research aims to study fluconazole (FNZ)-solvent interactions in pure solvents through theoretical and experimental solvatochromism. This study showed a bathochromic shift as the polarity of the solvent increases, where the excited state of FNZ is of higher polarity and lower energy than that of the ground state. The multiparametric statistical analysis highlighted solvent polarizability, dispersion, and electronic induction as solvent parameters of great importance, with the basicity of solvent and hydrogen bond acceptor capacity as having certain relevance. The thermochromic effect was also determined by exposing the three pKa values of FNZ. In conclusion, this study shows the importance of the π-π stacking interaction of the FNZ dihalogenated phenyl ring, the solvent basicity for the hydroxyl group, and its acidity for the N4' of one of the triazoles stand out, as well as the acid-base equilibria involving the -OH group and the two N4'.
Fil: Olivares, Fernando Gabriel. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina
Fil: Lazcano, Francisco Gabriel. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina
Fil: Castillo, Marcelo Omar. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina
Fil: Barúa, María Gloria. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina
Fil: Escalada, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina
Fil: Pinto Vitorino, Graciela. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina - Materia
-
FLUCONAZOLE
SOLVATOCHROMISM
THERMOCHROMISM
TD-DFT
FLUCONAZOLE
SOLVATOCHROMISM
THERMOCHROMISM - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by/2.5/ar/
- Repositorio
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/225159
Ver los metadatos del registro completo
| id |
CONICETDig_52d0062d9e9a0ffb84d1c909d348dd8b |
|---|---|
| oai_identifier_str |
oai:ri.conicet.gov.ar:11336/225159 |
| network_acronym_str |
CONICETDig |
| repository_id_str |
3498 |
| network_name_str |
CONICET Digital (CONICET) |
| spelling |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical StudyOlivares, Fernando GabrielLazcano, Francisco GabrielCastillo, Marcelo OmarBarúa, María GloriaEscalada, Juan PabloPinto Vitorino, GracielaFLUCONAZOLESOLVATOCHROMISMTHERMOCHROMISMTD-DFTFLUCONAZOLESOLVATOCHROMISMTHERMOCHROMISMhttps://purl.org/becyt/ford/1.2https://purl.org/becyt/ford/1This research aims to study fluconazole (FNZ)-solvent interactions in pure solvents through theoretical and experimental solvatochromism. This study showed a bathochromic shift as the polarity of the solvent increases, where the excited state of FNZ is of higher polarity and lower energy than that of the ground state. The multiparametric statistical analysis highlighted solvent polarizability, dispersion, and electronic induction as solvent parameters of great importance, with the basicity of solvent and hydrogen bond acceptor capacity as having certain relevance. The thermochromic effect was also determined by exposing the three pKa values of FNZ. In conclusion, this study shows the importance of the π-π stacking interaction of the FNZ dihalogenated phenyl ring, the solvent basicity for the hydroxyl group, and its acidity for the N4' of one of the triazoles stand out, as well as the acid-base equilibria involving the -OH group and the two N4'.Fil: Olivares, Fernando Gabriel. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; ArgentinaFil: Lazcano, Francisco Gabriel. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; ArgentinaFil: Castillo, Marcelo Omar. Universidad Nacional de la Patagonia "San Juan Bosco"; ArgentinaFil: Barúa, María Gloria. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; ArgentinaFil: Escalada, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; ArgentinaFil: Pinto Vitorino, Graciela. Universidad Nacional de la Patagonia "San Juan Bosco"; ArgentinaSociedade Brasileira de Química2023-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/225159Olivares, Fernando Gabriel; Lazcano, Francisco Gabriel; Castillo, Marcelo Omar; Barúa, María Gloria; Escalada, Juan Pablo; et al.; Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study; Sociedade Brasileira de Química; Journal of the Brazilian Chemical Society; 34; 10; 4-2023; 1380-13970103-50531678-4790CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://s3.sa-east-1.amazonaws.com/static.sites.sbq.org.br/jbcs.sbq.org.br/pdf/2022-0343AR.pdfinfo:eu-repo/semantics/altIdentifier/doi/10.21577/0103-5053.20230050info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:53:41Zoai:ri.conicet.gov.ar:11336/225159instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 09:53:41.388CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| title |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| spellingShingle |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study Olivares, Fernando Gabriel FLUCONAZOLE SOLVATOCHROMISM THERMOCHROMISM TD-DFT FLUCONAZOLE SOLVATOCHROMISM THERMOCHROMISM |
| title_short |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| title_full |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| title_fullStr |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| title_full_unstemmed |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| title_sort |
Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study |
| dc.creator.none.fl_str_mv |
Olivares, Fernando Gabriel Lazcano, Francisco Gabriel Castillo, Marcelo Omar Barúa, María Gloria Escalada, Juan Pablo Pinto Vitorino, Graciela |
| author |
Olivares, Fernando Gabriel |
| author_facet |
Olivares, Fernando Gabriel Lazcano, Francisco Gabriel Castillo, Marcelo Omar Barúa, María Gloria Escalada, Juan Pablo Pinto Vitorino, Graciela |
| author_role |
author |
| author2 |
Lazcano, Francisco Gabriel Castillo, Marcelo Omar Barúa, María Gloria Escalada, Juan Pablo Pinto Vitorino, Graciela |
| author2_role |
author author author author author |
| dc.subject.none.fl_str_mv |
FLUCONAZOLE SOLVATOCHROMISM THERMOCHROMISM TD-DFT FLUCONAZOLE SOLVATOCHROMISM THERMOCHROMISM |
| topic |
FLUCONAZOLE SOLVATOCHROMISM THERMOCHROMISM TD-DFT FLUCONAZOLE SOLVATOCHROMISM THERMOCHROMISM |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.2 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
This research aims to study fluconazole (FNZ)-solvent interactions in pure solvents through theoretical and experimental solvatochromism. This study showed a bathochromic shift as the polarity of the solvent increases, where the excited state of FNZ is of higher polarity and lower energy than that of the ground state. The multiparametric statistical analysis highlighted solvent polarizability, dispersion, and electronic induction as solvent parameters of great importance, with the basicity of solvent and hydrogen bond acceptor capacity as having certain relevance. The thermochromic effect was also determined by exposing the three pKa values of FNZ. In conclusion, this study shows the importance of the π-π stacking interaction of the FNZ dihalogenated phenyl ring, the solvent basicity for the hydroxyl group, and its acidity for the N4' of one of the triazoles stand out, as well as the acid-base equilibria involving the -OH group and the two N4'. Fil: Olivares, Fernando Gabriel. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina Fil: Lazcano, Francisco Gabriel. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina Fil: Castillo, Marcelo Omar. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina Fil: Barúa, María Gloria. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina Fil: Escalada, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de la Patagonia Austral. Unidad Académica Río Gallegos; Argentina Fil: Pinto Vitorino, Graciela. Universidad Nacional de la Patagonia "San Juan Bosco"; Argentina |
| description |
This research aims to study fluconazole (FNZ)-solvent interactions in pure solvents through theoretical and experimental solvatochromism. This study showed a bathochromic shift as the polarity of the solvent increases, where the excited state of FNZ is of higher polarity and lower energy than that of the ground state. The multiparametric statistical analysis highlighted solvent polarizability, dispersion, and electronic induction as solvent parameters of great importance, with the basicity of solvent and hydrogen bond acceptor capacity as having certain relevance. The thermochromic effect was also determined by exposing the three pKa values of FNZ. In conclusion, this study shows the importance of the π-π stacking interaction of the FNZ dihalogenated phenyl ring, the solvent basicity for the hydroxyl group, and its acidity for the N4' of one of the triazoles stand out, as well as the acid-base equilibria involving the -OH group and the two N4'. |
| publishDate |
2023 |
| dc.date.none.fl_str_mv |
2023-04 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion http://purl.org/coar/resource_type/c_6501 info:ar-repo/semantics/articulo |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/11336/225159 Olivares, Fernando Gabriel; Lazcano, Francisco Gabriel; Castillo, Marcelo Omar; Barúa, María Gloria; Escalada, Juan Pablo; et al.; Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study; Sociedade Brasileira de Química; Journal of the Brazilian Chemical Society; 34; 10; 4-2023; 1380-1397 0103-5053 1678-4790 CONICET Digital CONICET |
| url |
http://hdl.handle.net/11336/225159 |
| identifier_str_mv |
Olivares, Fernando Gabriel; Lazcano, Francisco Gabriel; Castillo, Marcelo Omar; Barúa, María Gloria; Escalada, Juan Pablo; et al.; Solvatochromism and Thermochromism of Fluconazole: An Experimental and Theoretical Study; Sociedade Brasileira de Química; Journal of the Brazilian Chemical Society; 34; 10; 4-2023; 1380-1397 0103-5053 1678-4790 CONICET Digital CONICET |
| dc.language.none.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/https://s3.sa-east-1.amazonaws.com/static.sites.sbq.org.br/jbcs.sbq.org.br/pdf/2022-0343AR.pdf info:eu-repo/semantics/altIdentifier/doi/10.21577/0103-5053.20230050 |
| dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by/2.5/ar/ |
| eu_rights_str_mv |
openAccess |
| rights_invalid_str_mv |
https://creativecommons.org/licenses/by/2.5/ar/ |
| dc.format.none.fl_str_mv |
application/pdf application/pdf application/pdf application/pdf application/pdf |
| dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
| publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
| dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
| reponame_str |
CONICET Digital (CONICET) |
| collection |
CONICET Digital (CONICET) |
| instname_str |
Consejo Nacional de Investigaciones Científicas y Técnicas |
| repository.name.fl_str_mv |
CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
| repository.mail.fl_str_mv |
dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
| _version_ |
1842269241448857600 |
| score |
12.885934 |