The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study

Autores
Espitia Cogollo, Edeimis; Jios, Eliana; Hidalgo, Alejandra; Ulic, Sonia Elizabeth; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Jios, Jorge Luis
Año de publicación
2021
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new perfluoromethylated vinylogous amide, (Z)-4,4,4-trifluoro-1-(2- hydroxyphenyl)-3-(2-methoxyethylamino)-2-buten-1-one, is chosen as an example to investigate the bonding interactions in solid state. The Z, s-cis form is the dominant conformation in both solution and solid state. Intramolecular hydrogen bonding determines this conformational preference in a nonpolar solvent (NMR spectra). Carbonyl and phenol groups are sensitive to the intra- and intermolecular contacts (vibrational spectra). The supramolecular assembly (X-ray diffraction) is governed by NH⋯O and OH⋯O strong intermolecular hydrogen bonds giving rise to center-symmetric R2 2(16) and R2 2(12) graph-set motifs. The -stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).
Centro de Química Inorgánica
Materia
Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-nd/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/159607
Acceder
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oai_identifier_str oai:sedici.unlp.edu.ar:10915/159607
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case studyEspitia Cogollo, EdeimisJios, ElianaHidalgo, AlejandraUlic, Sonia ElizabethEcheverría, Gustavo AlbertoPiro, Oscar EnriqueJios, Jorge LuisQuímicaHirshfeld analysisX-ray diffractionHydrogen bondingVinylogous amideA new perfluoromethylated vinylogous amide, (Z)-4,4,4-trifluoro-1-(2- hydroxyphenyl)-3-(2-methoxyethylamino)-2-buten-1-one, is chosen as an example to investigate the bonding interactions in solid state. The Z, s-cis form is the dominant conformation in both solution and solid state. Intramolecular hydrogen bonding determines this conformational preference in a nonpolar solvent (NMR spectra). Carbonyl and phenol groups are sensitive to the intra- and intermolecular contacts (vibrational spectra). The supramolecular assembly (X-ray diffraction) is governed by NH⋯O and OH⋯O strong intermolecular hydrogen bonds giving rise to center-symmetric R2 2(16) and R2 2(12) graph-set motifs. The -stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).Centro de Química Inorgánica2021-02-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfhttp://sedici.unlp.edu.ar/handle/10915/159607enginfo:eu-repo/semantics/altIdentifier/issn/1521-4079info:eu-repo/semantics/altIdentifier/doi/10.1002/crat.202000162info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-nd/4.0/Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-10-22T17:22:37Zoai:sedici.unlp.edu.ar:10915/159607Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-10-22 17:22:37.957SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
title The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
spellingShingle The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
Espitia Cogollo, Edeimis
Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
title_short The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
title_full The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
title_fullStr The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
title_full_unstemmed The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
title_sort The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
dc.creator.none.fl_str_mv Espitia Cogollo, Edeimis
Jios, Eliana
Hidalgo, Alejandra
Ulic, Sonia Elizabeth
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
author Espitia Cogollo, Edeimis
author_facet Espitia Cogollo, Edeimis
Jios, Eliana
Hidalgo, Alejandra
Ulic, Sonia Elizabeth
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
author_role author
author2 Jios, Eliana
Hidalgo, Alejandra
Ulic, Sonia Elizabeth
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
topic Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
dc.description.none.fl_txt_mv A new perfluoromethylated vinylogous amide, (Z)-4,4,4-trifluoro-1-(2- hydroxyphenyl)-3-(2-methoxyethylamino)-2-buten-1-one, is chosen as an example to investigate the bonding interactions in solid state. The Z, s-cis form is the dominant conformation in both solution and solid state. Intramolecular hydrogen bonding determines this conformational preference in a nonpolar solvent (NMR spectra). Carbonyl and phenol groups are sensitive to the intra- and intermolecular contacts (vibrational spectra). The supramolecular assembly (X-ray diffraction) is governed by NH⋯O and OH⋯O strong intermolecular hydrogen bonds giving rise to center-symmetric R2 2(16) and R2 2(12) graph-set motifs. The -stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).
Centro de Química Inorgánica
description A new perfluoromethylated vinylogous amide, (Z)-4,4,4-trifluoro-1-(2- hydroxyphenyl)-3-(2-methoxyethylamino)-2-buten-1-one, is chosen as an example to investigate the bonding interactions in solid state. The Z, s-cis form is the dominant conformation in both solution and solid state. Intramolecular hydrogen bonding determines this conformational preference in a nonpolar solvent (NMR spectra). Carbonyl and phenol groups are sensitive to the intra- and intermolecular contacts (vibrational spectra). The supramolecular assembly (X-ray diffraction) is governed by NH⋯O and OH⋯O strong intermolecular hydrogen bonds giving rise to center-symmetric R2 2(16) and R2 2(12) graph-set motifs. The -stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).
publishDate 2021
dc.date.none.fl_str_mv 2021-02-11
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/10915/159607
url http://sedici.unlp.edu.ar/handle/10915/159607
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1521-4079
info:eu-repo/semantics/altIdentifier/doi/10.1002/crat.202000162
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-nd/4.0/
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0)
dc.format.none.fl_str_mv application/pdf
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
instname:Universidad Nacional de La Plata
instacron:UNLP
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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score 12.982451

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