The Bonding Interactions in Fluorinated Vinylogous Amides: A CF3-Substituted Carbonyl-β-Aminoenone as a Case Study

ESPITIA COGOLLO, EDEIMIS; ULIC, SONIA ELIZABETH; JIOS, JORGE LUIS; JIOS, ELIANA; ECHEVERRÍA, GUSTAVO ALBERTO; HIDALGO, ALEJANDRA; PIRO, OSCAR ENRIQUE

CRYSTAL RESEARCH AND TECHNOLOGY

WILEY-V C H VERLAG GMBH

Año: 2020 vol. 56

0232-1300

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 (Formula presented.) and (Formula presented.) graph-set motifs. The π-stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).