A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing

Autores
Alcívar León, Christian David; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Ulic, Sonia Elizabeth; Jios, Jorge Luis
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The new 3-methyl-2-trifluoromethylchromone (1) and 3-bromomethyl-2-trifluoromethylchromone (2) compounds were synthesized and characterized by vibrational (IR, Raman), UV–Vis and NMR (1H, 13C and 19F) spectroscopy and MS spectrometry. The crystal structures of 1 and 2 were determined by X-ray diffraction methods. Both compounds crystallize in the monoclinic P21/c space group with Z = 4 molecules per unit cell. The structures were solved from 1423 (1) and 1856 (2) reflections with I > 2σ (I) and refined by full-matrix least-squares to agreement R1-values of 0.0403 (1) and 0.0554 (2). Because of π-bonding delocalization, the organic molecular skeletons are planar and the molecular bonding structures can be described by formally single, double and resonant bonds. In 2, the single bond CF3 group revealed a strong rotational disorder around the C single bond CF3 bond, which could be explained in terms of four split positions with about uniform angular distribution. The vibrational, electronic and NMR, spectra were discussed and assigned with the assistance of DFT calculations.
Centro de Química Inorgánica
Instituto de Física La Plata
Facultad de Ciencias Exactas
Materia
Ciencias Exactas
2-Trifluoromethy
lchromones
Quantum chemical calculations
Spectroscopic properties
Single crystal
X-ray diffraction
Nivel de accesibilidad
acceso abierto
Condiciones de uso
http://creativecommons.org/licenses/by-nc-sa/4.0/
Repositorio
SEDICI (UNLP)
Institución
Universidad Nacional de La Plata
OAI Identificador
oai:sedici.unlp.edu.ar:10915/108445
Acceder
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oai_identifier_str oai:sedici.unlp.edu.ar:10915/108445
network_acronym_str SEDICI
repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packingAlcívar León, Christian DavidEcheverría, Gustavo AlbertoPiro, Oscar EnriqueUlic, Sonia ElizabethJios, Jorge LuisCiencias Exactas2-TrifluoromethylchromonesQuantum chemical calculationsSpectroscopic propertiesSingle crystalX-ray diffractionThe new 3-methyl-2-trifluoromethylchromone (1) and 3-bromomethyl-2-trifluoromethylchromone (2) compounds were synthesized and characterized by vibrational (IR, Raman), UV–Vis and NMR (<sup>1</sup>H, <sup>13</sup>C and <sup>19</sup>F) spectroscopy and MS spectrometry. The crystal structures of 1 and 2 were determined by X-ray diffraction methods. Both compounds crystallize in the monoclinic P2<sub>1</sub>/c space group with Z = 4 molecules per unit cell. The structures were solved from 1423 (1) and 1856 (2) reflections with I > 2σ (I) and refined by full-matrix least-squares to agreement R1-values of 0.0403 (1) and 0.0554 (2). Because of π-bonding delocalization, the organic molecular skeletons are planar and the molecular bonding structures can be described by formally single, double and resonant bonds. In 2, the single bond CF<sub>3</sub> group revealed a strong rotational disorder around the C single bond CF<sub>3</sub> bond, which could be explained in terms of four split positions with about uniform angular distribution. The vibrational, electronic and NMR, spectra were discussed and assigned with the assistance of DFT calculations.Centro de Química InorgánicaInstituto de Física La PlataFacultad de Ciencias Exactas2015info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf1358-1370http://sedici.unlp.edu.ar/handle/10915/108445enginfo:eu-repo/semantics/altIdentifier/issn/1386-1425info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2014.10.022info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by-nc-sa/4.0/Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)reponame:SEDICI (UNLP)instname:Universidad Nacional de La Platainstacron:UNLP2025-10-22T17:05:30Zoai:sedici.unlp.edu.ar:10915/108445Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-10-22 17:05:30.596SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
title A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
spellingShingle A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
Alcívar León, Christian David
Ciencias Exactas
2-Trifluoromethy
lchromones
Quantum chemical calculations
Spectroscopic properties
Single crystal
X-ray diffraction
title_short A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
title_full A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
title_fullStr A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
title_full_unstemmed A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
title_sort A detailed experimental and theoretical study of two novel substituted trifluoromethylchromones : The influence of the bulky bromine atom on the crystal packing
dc.creator.none.fl_str_mv Alcívar León, Christian David
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Ulic, Sonia Elizabeth
Jios, Jorge Luis
author Alcívar León, Christian David
author_facet Alcívar León, Christian David
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Ulic, Sonia Elizabeth
Jios, Jorge Luis
author_role author
author2 Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Ulic, Sonia Elizabeth
Jios, Jorge Luis
author2_role author
author
author
author
dc.subject.none.fl_str_mv Ciencias Exactas
2-Trifluoromethy
lchromones
Quantum chemical calculations
Spectroscopic properties
Single crystal
X-ray diffraction
topic Ciencias Exactas
2-Trifluoromethy
lchromones
Quantum chemical calculations
Spectroscopic properties
Single crystal
X-ray diffraction
dc.description.none.fl_txt_mv The new 3-methyl-2-trifluoromethylchromone (1) and 3-bromomethyl-2-trifluoromethylchromone (2) compounds were synthesized and characterized by vibrational (IR, Raman), UV–Vis and NMR (<sup>1</sup>H, <sup>13</sup>C and <sup>19</sup>F) spectroscopy and MS spectrometry. The crystal structures of 1 and 2 were determined by X-ray diffraction methods. Both compounds crystallize in the monoclinic P2<sub>1</sub>/c space group with Z = 4 molecules per unit cell. The structures were solved from 1423 (1) and 1856 (2) reflections with I > 2σ (I) and refined by full-matrix least-squares to agreement R1-values of 0.0403 (1) and 0.0554 (2). Because of π-bonding delocalization, the organic molecular skeletons are planar and the molecular bonding structures can be described by formally single, double and resonant bonds. In 2, the single bond CF<sub>3</sub> group revealed a strong rotational disorder around the C single bond CF<sub>3</sub> bond, which could be explained in terms of four split positions with about uniform angular distribution. The vibrational, electronic and NMR, spectra were discussed and assigned with the assistance of DFT calculations.
Centro de Química Inorgánica
Instituto de Física La Plata
Facultad de Ciencias Exactas
description The new 3-methyl-2-trifluoromethylchromone (1) and 3-bromomethyl-2-trifluoromethylchromone (2) compounds were synthesized and characterized by vibrational (IR, Raman), UV–Vis and NMR (<sup>1</sup>H, <sup>13</sup>C and <sup>19</sup>F) spectroscopy and MS spectrometry. The crystal structures of 1 and 2 were determined by X-ray diffraction methods. Both compounds crystallize in the monoclinic P2<sub>1</sub>/c space group with Z = 4 molecules per unit cell. The structures were solved from 1423 (1) and 1856 (2) reflections with I > 2σ (I) and refined by full-matrix least-squares to agreement R1-values of 0.0403 (1) and 0.0554 (2). Because of π-bonding delocalization, the organic molecular skeletons are planar and the molecular bonding structures can be described by formally single, double and resonant bonds. In 2, the single bond CF<sub>3</sub> group revealed a strong rotational disorder around the C single bond CF<sub>3</sub> bond, which could be explained in terms of four split positions with about uniform angular distribution. The vibrational, electronic and NMR, spectra were discussed and assigned with the assistance of DFT calculations.
publishDate 2015
dc.date.none.fl_str_mv 2015
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/10915/108445
url http://sedici.unlp.edu.ar/handle/10915/108445
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/issn/1386-1425
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.saa.2014.10.022
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc-sa/4.0/
Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International (CC BY-NC-SA 4.0)
dc.format.none.fl_str_mv application/pdf
1358-1370
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instname:Universidad Nacional de La Plata
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reponame_str SEDICI (UNLP)
collection SEDICI (UNLP)
instname_str Universidad Nacional de La Plata
instacron_str UNLP
institution UNLP
repository.name.fl_str_mv SEDICI (UNLP) - Universidad Nacional de La Plata
repository.mail.fl_str_mv alira@sedici.unlp.edu.ar
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