Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivatives
- Autores
- Espitia Cogollo, Edeimis; Piro, Oscar Enrique; Echeverría, Gustavo Alberto; Tuttolomondo, M. E.; Pérez, 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 the o-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. Compounds 1 and 4 have similar structural motifs with N–H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along the a-axis. For 2, 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 compound 3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of 3, 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.
Centro de Química Inorgánica - Materia
-
Química
Ciencias Exactas
X-ray crystal structure
molecular interactions
NBO intermolecular energies
Hirshfeld surface analysis
Pixel energies
vibrational spectroscopy - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- http://creativecommons.org/licenses/by/4.0/
- Repositorio
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/141466
Ver los metadatos del registro completo
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Hydrogen bonding interactions in fluorinated 1,2,3-triazole derivativesEspitia Cogollo, EdeimisPiro, Oscar EnriqueEcheverría, Gustavo AlbertoTuttolomondo, M. E.Pérez, HiramJios, Jorge LuisUlic, Sonia ElizabethQuímicaCiencias ExactasX-ray crystal structuremolecular interactionsNBO intermolecular energiesHirshfeld surface analysisPixel energiesvibrational spectroscopyThe 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 the o-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. Compounds 1 and 4 have similar structural motifs with N–H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along the a-axis. For 2, 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 compound 3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of 3, 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.Centro de Química Inorgánica2020-09-28info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf16006-16019http://sedici.unlp.edu.ar/handle/10915/141466enginfo:eu-repo/semantics/altIdentifier/issn/1144-0546info:eu-repo/semantics/altIdentifier/issn/1369-9261info:eu-repo/semantics/altIdentifier/doi/10.1039/d0nj02914ainfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/4.0/Creative Commons Attribution 4.0 International (CC BY 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:32:07Zoai:sedici.unlp.edu.ar:10915/141466Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:32:07.307SEDICI (UNLP) - Universidad Nacional de La Platafalse |
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 Química Ciencias Exactas X-ray crystal structure molecular interactions NBO intermolecular energies Hirshfeld surface analysis Pixel energies vibrational spectroscopy |
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, M. E. Pérez, Hiram Jios, Jorge Luis Ulic, Sonia Elizabeth |
author |
Espitia Cogollo, Edeimis |
author_facet |
Espitia Cogollo, Edeimis Piro, Oscar Enrique Echeverría, Gustavo Alberto Tuttolomondo, M. E. Pérez, Hiram Jios, Jorge Luis Ulic, Sonia Elizabeth |
author_role |
author |
author2 |
Piro, Oscar Enrique Echeverría, Gustavo Alberto Tuttolomondo, M. E. Pérez, Hiram Jios, Jorge Luis Ulic, Sonia Elizabeth |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
Química Ciencias Exactas X-ray crystal structure molecular interactions NBO intermolecular energies Hirshfeld surface analysis Pixel energies vibrational spectroscopy |
topic |
Química Ciencias Exactas X-ray crystal structure molecular interactions NBO intermolecular energies Hirshfeld surface analysis Pixel energies vibrational spectroscopy |
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 the o-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. Compounds 1 and 4 have similar structural motifs with N–H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along the a-axis. For 2, 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 compound 3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of 3, 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. Centro de Química Inorgánica |
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 the o-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. Compounds 1 and 4 have similar structural motifs with N–H⋯O hydrogen bonds connecting amino and carbonyl groups of neighboring molecules in a chain along the a-axis. For 2, 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 compound 3, the crystallization water molecule dominates the hydrogen bonding interactions, which associates three molecules of 3, 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 |
2020-09-28 |
dc.type.none.fl_str_mv |
info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion Articulo 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://sedici.unlp.edu.ar/handle/10915/141466 |
url |
http://sedici.unlp.edu.ar/handle/10915/141466 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/issn/1144-0546 info:eu-repo/semantics/altIdentifier/issn/1369-9261 info:eu-repo/semantics/altIdentifier/doi/10.1039/d0nj02914a |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) |
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openAccess |
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http://creativecommons.org/licenses/by/4.0/ Creative Commons Attribution 4.0 International (CC BY 4.0) |
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application/pdf 16006-16019 |
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