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

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...

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Autores principales: Espitia Cogollo, Edeimis, Jios, Eliana, Hidalgo, Alejandra, Ulic, Sonia Elizabeth, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, Jios, Jorge Luis
Formato: Articulo
Lenguaje:Inglés
Publicado: 2021
Materias:
Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/159607
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-159607
record_format dspace
spelling I19-R120-10915-1596072023-10-31T20:07:52Z http://sedici.unlp.edu.ar/handle/10915/159607 The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study Espitia Cogollo, Edeimis Jios, Eliana Hidalgo, Alejandra Ulic, Sonia Elizabeth Echeverría, Gustavo Alberto Piro, Oscar Enrique Jios, Jorge Luis 2021-02-11 2023-10-31T14:31:59Z en Química Hirshfeld analysis X-ray diffraction Hydrogen bonding Vinylogous amide 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 Articulo Articulo http://creativecommons.org/licenses/by-nc-nd/4.0/ Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) application/pdf
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
spellingShingle Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
Espitia Cogollo, Edeimis
Jios, Eliana
Hidalgo, Alejandra
Ulic, Sonia Elizabeth
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
topic_facet Química
Hirshfeld analysis
X-ray diffraction
Hydrogen bonding
Vinylogous amide
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).
format Articulo
Articulo
author Espitia Cogollo, Edeimis
Jios, Eliana
Hidalgo, Alejandra
Ulic, Sonia Elizabeth
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
author_facet Espitia Cogollo, Edeimis
Jios, Eliana
Hidalgo, Alejandra
Ulic, Sonia Elizabeth
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Jios, Jorge Luis
author_sort Espitia Cogollo, Edeimis
title The bonding interactions in fluorinated vinylogous amides: a CF3-substituted carbonyl β-aminoenone as a case study
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 bonding interactions in fluorinated vinylogous amides: a cf3-substituted carbonyl β-aminoenone as a case study
publishDate 2021
url http://sedici.unlp.edu.ar/handle/10915/159607
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