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The Bonding Interactions in Fluorinated Vinylogous Amides: A CF 3 ‐Substituted Carbonyl‐β‐Aminoenone as a Case Study
Author(s) -
Espitia Cogollo Edeimis,
Jios Eliana,
Hidalgo Alejandra,
Ulic Sonia Elizabeth,
Echeverría Gustavo Alberto,
Piro Oscar Enrique,
Jios Jorge Luis
Publication year - 2021
Publication title -
crystal research and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.377
H-Index - 64
eISSN - 1521-4079
pISSN - 0232-1300
DOI - 10.1002/crat.202000162
Subject(s) - chemistry , intermolecular force , hydrogen bond , intramolecular force , stacking , supramolecular chemistry , amide , crystallography , solvent , solid state , stereochemistry , molecule , crystal structure , organic chemistry
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‐symmetricR 2 2 ( 16 )andR 2 2 ( 12 )graph‐set motifs. The π‐stacking, F⋯H and F⋯F interactions are also discussed (Hirshfeld analysis).