Articulo
The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
Registro en:
issn:1144-0546
issn:1369-9261
Autor
Alcívar León, Christian David
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Ulic, Sonia Elizabeth
Jios, Jorge Luis
Pereañez, Jaime Andrés
Henao Castañeda, Isabel Cristina
Pérez, Hiram
Institución
Resumen
The intermolecular interactions in the solid state and the spectroscopic vibrational, electronic and NMR properties of new 3-methyl-substituted-2-trifluoromethylchromone derivatives with –CN (1), –NO₂ (2), –OH (3) and –NH₂ (4) groups were discussed with the assistance of DFT calculations. The crystal structures of compounds 1–3 were determined by X-ray diffraction showing molecular ribbons for compounds 1 and 2, and dimers via O–H⋯O=C hydrogen bonds for 3. Hirshfeld surfaces and the corresponding fingerprint plots, as well as the electrostatic potentials mapped on the surfaces revealed C–H⋯O and C–H⋯F hydrogen bonds, and π⋯π stacking as the main cooperative driving forces for building supramolecular architectures in all compounds. The C–H⋯π and C=O⋯π interactions also contribute to stabilizing the crystal structures of 1 and 2. A further analysis of Hirshfeld surfaces was performed using the enrichment ratio as a new descriptor to determine the likelihood of chemical species to establish specific interactions in the molecular packing. The lattice energies of the crystal structures and several intermolecular contacts present in different molecular pairs were also quantified. Molecular docking studies showed the interaction of the title compounds with the catalytic site of PLA₂ (PDB code 2QOG) from <i>Crotalus durissus terrificus</i>, and suggested that the investigated compounds could inhibit toxic effects of snake venom. Instituto de Física La Plata Centro de Química Inorgánica Planta Piloto Multipropósito - Laboratorio de Servicios a la Industria y al Sistema Científico