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
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/141466

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network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling 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
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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)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/4.0/
Creative Commons Attribution 4.0 International (CC BY 4.0)
dc.format.none.fl_str_mv application/pdf
16006-16019
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reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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