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
- Institución
- Universidad Nacional de La Plata
- OAI Identificador
- oai:sedici.unlp.edu.ar:10915/148038
Ver los metadatos del registro completo
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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 http://purl.org/coar/resource_type/c_6501 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 |
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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) |
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openAccess |
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