The Bonding Interactions in Fluorinated Vinylogous Amides: A CF3-Substituted Carbonyl-β-Aminoenone as a Case Study
Edeimis Espitia Cogollo
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Search for more papers by this authorEliana Jios
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Search for more papers by this authorAlejandra Hidalgo
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Search for more papers by this authorCorresponding Author
Sonia Elizabeth Ulic
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Departamento de Ciencias Básicas, Universidad Nacional de Luján, Rutas 5 y 7, 6700 Luján, Buenos Aires, Argentina
E-mail: sonia@quimica.unlp.edu.ar; jljios@quimica.unlp.edu.ar
Search for more papers by this authorGustavo Alberto Echeverría
Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e IFLP (CONICET, CCT-La Plata), C. C. 67, La Plata, 1900 Argentina
Search for more papers by this authorOscar Enrique Piro
Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e IFLP (CONICET, CCT-La Plata), C. C. 67, La Plata, 1900 Argentina
Search for more papers by this authorCorresponding Author
Jorge Luis Jios
Laboratorio UPL (UNLP-CIC), Camino Centenario e/505 y 508, M.B. Gonnet, Buenos Aires, 1897 Argentina
Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, La Plata, 1900 Argentina
E-mail: sonia@quimica.unlp.edu.ar; jljios@quimica.unlp.edu.ar
Search for more papers by this authorEdeimis Espitia Cogollo
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Search for more papers by this authorEliana Jios
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Search for more papers by this authorAlejandra Hidalgo
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Search for more papers by this authorCorresponding Author
Sonia Elizabeth Ulic
CEQUINOR (CONICET-UNLP), Facultad de Ciencias Exactas, Universidad Nacional de La Plata, Bv. 120 N° 1465, La Plata, 1900 Argentina
Departamento de Ciencias Básicas, Universidad Nacional de Luján, Rutas 5 y 7, 6700 Luján, Buenos Aires, Argentina
E-mail: sonia@quimica.unlp.edu.ar; jljios@quimica.unlp.edu.ar
Search for more papers by this authorGustavo Alberto Echeverría
Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e IFLP (CONICET, CCT-La Plata), C. C. 67, La Plata, 1900 Argentina
Search for more papers by this authorOscar Enrique Piro
Departamento de Física, Facultad de Ciencias Exactas, Universidad Nacional de La Plata e IFLP (CONICET, CCT-La Plata), C. C. 67, La Plata, 1900 Argentina
Search for more papers by this authorCorresponding Author
Jorge Luis Jios
Laboratorio UPL (UNLP-CIC), Camino Centenario e/505 y 508, M.B. Gonnet, Buenos Aires, 1897 Argentina
Departamento de Química, Facultad de Ciencias Exactas, Universidad Nacional de La Plata, 47 esq. 115, La Plata, 1900 Argentina
E-mail: sonia@quimica.unlp.edu.ar; jljios@quimica.unlp.edu.ar
Search for more papers by this authorAbstract
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 and graph-set motifs. The π-stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).
Conflict of Interest
The authors declare no conflict of interest.
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