Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
- Autores
- Espitia Cogollo, Edeimis; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Tuttolomondo, María Eugenia; Perez, Hiram; Jios, Jorge Luis; Ulic, Sonia Elizabeth
- Año de publicación
- 2020
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = -H,2: R = -NO2,3: R = -CH3,4: R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol-keto/keto-enol tautomerism on theo-hydroxyacetophenone moiety was analyzed in terms of the synergy between O-H⋯O intramolecular hydrogen bond strengthening and the enhancement of π delocalization within the pseudo ring. The preference of the enol-keto form was attributed to the aromatic stabilization energy. The proton in the triazole ring was located on the intermediate nitrogen atom, with no evidence of prototropy in the studied series. Compounds1and4have similar structural motifs with N-H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along thea-axis. For2, it was found that both oxygen atoms of the nitro substituent participate as acceptors, connecting adjacent molecules by hydrogen bonds through the N-H and O-H groups. In compound3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of3, giving rise to a three-dimensional H-bonding network. These intra and intermolecular interactions, which affect the absorption band locations of the involved groups, were also detected in the vibrational spectra of the studied triazoles.
Fil: Espitia Cogollo, Edeimis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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
Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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
Fil: Tuttolomondo, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Fil: Perez, Hiram. Universidad de La Habana; Cuba
Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas; Argentina
Fil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; Argentina - Materia
-
X-ray crystal structure
Molecular Interactions
Vibrational Spectroscopy
Pixel energies - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/143651
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Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivativesEspitia Cogollo, EdeimisPiro, Oscar EnriqueEcheverría, Gustavo AlbertoTuttolomondo, María EugeniaPerez, HiramJios, Jorge LuisUlic, Sonia ElizabethX-ray crystal structureMolecular InteractionsVibrational SpectroscopyPixel energieshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = -H,2: R = -NO2,3: R = -CH3,4: R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol-keto/keto-enol tautomerism on theo-hydroxyacetophenone moiety was analyzed in terms of the synergy between O-H⋯O intramolecular hydrogen bond strengthening and the enhancement of π delocalization within the pseudo ring. The preference of the enol-keto form was attributed to the aromatic stabilization energy. The proton in the triazole ring was located on the intermediate nitrogen atom, with no evidence of prototropy in the studied series. Compounds1and4have similar structural motifs with N-H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along thea-axis. For2, it was found that both oxygen atoms of the nitro substituent participate as acceptors, connecting adjacent molecules by hydrogen bonds through the N-H and O-H groups. In compound3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of3, giving rise to a three-dimensional H-bonding network. These intra and intermolecular interactions, which affect the absorption band locations of the involved groups, were also detected in the vibrational spectra of the studied triazoles.Fil: Espitia Cogollo, Edeimis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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; ArgentinaFil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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; ArgentinaFil: Tuttolomondo, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaFil: Perez, Hiram. Universidad de La Habana; CubaFil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas; ArgentinaFil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; ArgentinaRoyal Society of Chemistry2020-08-24info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/143651Espitia Cogollo, Edeimis; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Tuttolomondo, María Eugenia; Perez, Hiram; et al.; Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives; Royal Society of Chemistry; New Journal of Chemistry; 44; 37; 24-8-2020; 16006-160191144-05461369-9261CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2020/NJ/D0NJ02914Ainfo:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ02914Ainfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:43:29Zoai:ri.conicet.gov.ar:11336/143651instacron: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:34982025-09-29 09:43:29.48CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
title |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
spellingShingle |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives Espitia Cogollo, Edeimis X-ray crystal structure Molecular Interactions Vibrational Spectroscopy Pixel energies |
title_short |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
title_full |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
title_fullStr |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
title_full_unstemmed |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
title_sort |
Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives |
dc.creator.none.fl_str_mv |
Espitia Cogollo, Edeimis Piro, Oscar Enrique Echeverría, Gustavo Alberto Tuttolomondo, María Eugenia Perez, Hiram Jios, Jorge Luis Ulic, Sonia Elizabeth |
author |
Espitia Cogollo, Edeimis |
author_facet |
Espitia Cogollo, Edeimis Piro, Oscar Enrique Echeverría, Gustavo Alberto Tuttolomondo, María Eugenia Perez, Hiram Jios, Jorge Luis Ulic, Sonia Elizabeth |
author_role |
author |
author2 |
Piro, Oscar Enrique Echeverría, Gustavo Alberto Tuttolomondo, María Eugenia Perez, Hiram Jios, Jorge Luis Ulic, Sonia Elizabeth |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
X-ray crystal structure Molecular Interactions Vibrational Spectroscopy Pixel energies |
topic |
X-ray crystal structure Molecular Interactions Vibrational Spectroscopy Pixel energies |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = -H,2: R = -NO2,3: R = -CH3,4: R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol-keto/keto-enol tautomerism on theo-hydroxyacetophenone moiety was analyzed in terms of the synergy between O-H⋯O intramolecular hydrogen bond strengthening and the enhancement of π delocalization within the pseudo ring. The preference of the enol-keto form was attributed to the aromatic stabilization energy. The proton in the triazole ring was located on the intermediate nitrogen atom, with no evidence of prototropy in the studied series. Compounds1and4have similar structural motifs with N-H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along thea-axis. For2, it was found that both oxygen atoms of the nitro substituent participate as acceptors, connecting adjacent molecules by hydrogen bonds through the N-H and O-H groups. In compound3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of3, giving rise to a three-dimensional H-bonding network. These intra and intermolecular interactions, which affect the absorption band locations of the involved groups, were also detected in the vibrational spectra of the studied triazoles. Fil: Espitia Cogollo, Edeimis. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina Fil: Piro, Oscar Enrique. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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 Fil: Echeverría, Gustavo Alberto. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Física; Argentina. 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 Fil: Tuttolomondo, María Eugenia. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina Fil: Perez, Hiram. Universidad de La Habana; Cuba Fil: Jios, Jorge Luis. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Departamento de Química; Argentina. Provincia de Buenos Aires. Gobernación. Comisión de Investigaciones Científicas; Argentina Fil: Ulic, Sonia Elizabeth. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina. Universidad Nacional de Luján. Departamento de Ciencias Básicas; Argentina |
description |
The study of the intra- and intermolecular interactions in the solid state of four related fluorine-containing 1,2,3-triazole derivatives (1: R = -H,2: R = -NO2,3: R = -CH3,4: R = -Cl) was carried out using quantum chemical calculations, vibrational (IR and Raman) and solid phase UV-vis spectroscopy, and single-crystal X-ray diffraction methods. The enol-keto/keto-enol tautomerism on theo-hydroxyacetophenone moiety was analyzed in terms of the synergy between O-H⋯O intramolecular hydrogen bond strengthening and the enhancement of π delocalization within the pseudo ring. The preference of the enol-keto form was attributed to the aromatic stabilization energy. The proton in the triazole ring was located on the intermediate nitrogen atom, with no evidence of prototropy in the studied series. Compounds1and4have similar structural motifs with N-H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along thea-axis. For2, it was found that both oxygen atoms of the nitro substituent participate as acceptors, connecting adjacent molecules by hydrogen bonds through the N-H and O-H groups. In compound3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of3, giving rise to a three-dimensional H-bonding network. These intra and intermolecular interactions, which affect the absorption band locations of the involved groups, were also detected in the vibrational spectra of the studied triazoles. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-08-24 |
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/11336/143651 Espitia Cogollo, Edeimis; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Tuttolomondo, María Eugenia; Perez, Hiram; et al.; Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives; Royal Society of Chemistry; New Journal of Chemistry; 44; 37; 24-8-2020; 16006-16019 1144-0546 1369-9261 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/143651 |
identifier_str_mv |
Espitia Cogollo, Edeimis; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Tuttolomondo, María Eugenia; Perez, Hiram; et al.; Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives; Royal Society of Chemistry; New Journal of Chemistry; 44; 37; 24-8-2020; 16006-16019 1144-0546 1369-9261 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2020/NJ/D0NJ02914A info:eu-repo/semantics/altIdentifier/doi/10.1039/D0NJ02914A |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
eu_rights_str_mv |
openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
dc.format.none.fl_str_mv |
application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
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 |
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13.070432 |