The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state

Autores
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
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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 Crotalus durissus terrificus, 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
Materia
Física
Química
2-trifluoromethylchromones
solid state
non-covalent interactions
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by/3.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/148038

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network_name_str SEDICI (UNLP)
spelling The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid stateAlcívar León, Christian DavidEcheverría, Gustavo AlbertoPiro, Oscar EnriqueUlic, Sonia ElizabethJios, Jorge LuisPereañez, Jaime AndrésHenao Castañeda, Isabel CristinaPérez, HiramFísicaQuímica2-trifluoromethylchromonessolid statenon-covalent interactionsThe 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 PlataCentro de Química InorgánicaPlanta Piloto Multipropósito - Laboratorio de Servicios a la Industria y al Sistema Científico2017info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf14659-14674http://sedici.unlp.edu.ar/handle/10915/148038enginfo:eu-repo/semantics/altIdentifier/issn/1144-0546info:eu-repo/semantics/altIdentifier/issn/1369-9261info:eu-repo/semantics/altIdentifier/doi/10.1039/C7NJ00481Hinfo:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/Creative Commons Attribution 3.0 Unported (CC BY 3.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-09-29T11:37:53Zoai:sedici.unlp.edu.ar:10915/148038Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-09-29 11:37:53.424SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
title The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
spellingShingle The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
Alcívar León, Christian David
Física
Química
2-trifluoromethylchromones
solid state
non-covalent interactions
title_short The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
title_full The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
title_fullStr The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
title_full_unstemmed The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
title_sort The role of non-covalent interactions in some 2-trifluoromethylchromones in the solid state
dc.creator.none.fl_str_mv 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
author Alcívar León, Christian David
author_facet 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
author_role author
author2 Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Ulic, Sonia Elizabeth
Jios, Jorge Luis
Pereañez, Jaime Andrés
Henao Castañeda, Isabel Cristina
Pérez, Hiram
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Física
Química
2-trifluoromethylchromones
solid state
non-covalent interactions
topic Física
Química
2-trifluoromethylchromones
solid state
non-covalent interactions
dc.description.none.fl_txt_mv 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
description 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.
publishDate 2017
dc.date.none.fl_str_mv 2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
Articulo
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info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://sedici.unlp.edu.ar/handle/10915/148038
url http://sedici.unlp.edu.ar/handle/10915/148038
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1144-0546
info:eu-repo/semantics/altIdentifier/issn/1369-9261
info:eu-repo/semantics/altIdentifier/doi/10.1039/C7NJ00481H
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/
Creative Commons Attribution 3.0 Unported (CC BY 3.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/
Creative Commons Attribution 3.0 Unported (CC BY 3.0)
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repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
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