The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues

Autores
Delgado Espinosa, Zuly Yuliana; Saeed, Aamer; Mahmood, Shamsul; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; Erben, Mauricio Federico
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
4,7-Dimethyl-2H-chromen-2-one (1) and its novel sulfur analogue 4,7-dimethyl-2H-chromen-2-thione (2) were synthesized and fully characterized by spectroscopic methods and mass spectrometry. The crystal structure of compound 2 has been determined by X-ray diffraction methods, and it crystallizes in the monoclinic I2/m space group. The molecular skeleton lies in the crystallographic mirror plane, in agreement with the expected theoretical planarity enforced by extended π-bonding. The crystal packing of both compounds is characterized by the R22(8) motif formed by intermolecular C–H⋯X[double bond, length as m-dash]C (X = O and S) hydrogen-bonding interactions involving the 1-benzopyran-2-one/thione moiety, as also identified by Hirshfeld surface analysis. The vibrational properties have been studied by infrared and Raman spectroscopy complemented by quantum chemical calculations and normal coordinate analysis of the potential energy distribution. The UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations, showing a clear red-shift in the HOMO–LUMO electronic transition when the chromen-2-one ring is converted into chromen-2-thione.
Centro de Química Inorgánica
Instituto de Física La Plata
Materia
Física
Química
X-ray crystal structure
Hirshfeld analysis
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:10915/101000
Acceder
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oai_identifier_str oai:sedici.unlp.edu.ar:10915/101000
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repository_id_str 1329
network_name_str SEDICI (UNLP)
spelling The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analoguesDelgado Espinosa, Zuly YulianaSaeed, AamerMahmood, ShamsulEcheverría, Gustavo AlbertoPiro, Oscar EnriqueErben, Mauricio FedericoFísicaQuímicaX-ray crystal structureHirshfeld analysis4,7-Dimethyl-2H-chromen-2-one (1) and its novel sulfur analogue 4,7-dimethyl-2H-chromen-2-thione (2) were synthesized and fully characterized by spectroscopic methods and mass spectrometry. The crystal structure of compound 2 has been determined by X-ray diffraction methods, and it crystallizes in the monoclinic I2/m space group. The molecular skeleton lies in the crystallographic mirror plane, in agreement with the expected theoretical planarity enforced by extended π-bonding. The crystal packing of both compounds is characterized by the R22(8) motif formed by intermolecular C–H⋯X[double bond, length as m-dash]C (X = O and S) hydrogen-bonding interactions involving the 1-benzopyran-2-one/thione moiety, as also identified by Hirshfeld surface analysis. The vibrational properties have been studied by infrared and Raman spectroscopy complemented by quantum chemical calculations and normal coordinate analysis of the potential energy distribution. The UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations, showing a clear red-shift in the HOMO–LUMO electronic transition when the chromen-2-one ring is converted into chromen-2-thione.Centro de Química InorgánicaInstituto de Física La Plata2017-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArticulohttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdf5770-5783http://sedici.unlp.edu.ar/handle/10915/101000enginfo:eu-repo/semantics/altIdentifier/url/https://ri.conicet.gov.ar/11336/48645info:eu-repo/semantics/altIdentifier/issn/1144-0546info:eu-repo/semantics/altIdentifier/doi/10.1039/C7NJ01311Finfo:eu-repo/semantics/altIdentifier/hdl/11336/48645info: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:UNLP2025-12-23T11:22:16Zoai:sedici.unlp.edu.ar:10915/101000Institucionalhttp://sedici.unlp.edu.ar/Universidad públicaNo correspondehttp://sedici.unlp.edu.ar/oai/snrdalira@sedici.unlp.edu.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:13292025-12-23 11:22:16.754SEDICI (UNLP) - Universidad Nacional de La Platafalse
dc.title.none.fl_str_mv The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
title The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
spellingShingle The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
Delgado Espinosa, Zuly Yuliana
Física
Química
X-ray crystal structure
Hirshfeld analysis
title_short The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
title_full The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
title_fullStr The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
title_full_unstemmed The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
title_sort The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
dc.creator.none.fl_str_mv Delgado Espinosa, Zuly Yuliana
Saeed, Aamer
Mahmood, Shamsul
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Erben, Mauricio Federico
author Delgado Espinosa, Zuly Yuliana
author_facet Delgado Espinosa, Zuly Yuliana
Saeed, Aamer
Mahmood, Shamsul
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Erben, Mauricio Federico
author_role author
author2 Saeed, Aamer
Mahmood, Shamsul
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Erben, Mauricio Federico
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv Física
Química
X-ray crystal structure
Hirshfeld analysis
topic Física
Química
X-ray crystal structure
Hirshfeld analysis
dc.description.none.fl_txt_mv 4,7-Dimethyl-2H-chromen-2-one (1) and its novel sulfur analogue 4,7-dimethyl-2H-chromen-2-thione (2) were synthesized and fully characterized by spectroscopic methods and mass spectrometry. The crystal structure of compound 2 has been determined by X-ray diffraction methods, and it crystallizes in the monoclinic I2/m space group. The molecular skeleton lies in the crystallographic mirror plane, in agreement with the expected theoretical planarity enforced by extended π-bonding. The crystal packing of both compounds is characterized by the R22(8) motif formed by intermolecular C–H⋯X[double bond, length as m-dash]C (X = O and S) hydrogen-bonding interactions involving the 1-benzopyran-2-one/thione moiety, as also identified by Hirshfeld surface analysis. The vibrational properties have been studied by infrared and Raman spectroscopy complemented by quantum chemical calculations and normal coordinate analysis of the potential energy distribution. The UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations, showing a clear red-shift in the HOMO–LUMO electronic transition when the chromen-2-one ring is converted into chromen-2-thione.
Centro de Química Inorgánica
Instituto de Física La Plata
description 4,7-Dimethyl-2H-chromen-2-one (1) and its novel sulfur analogue 4,7-dimethyl-2H-chromen-2-thione (2) were synthesized and fully characterized by spectroscopic methods and mass spectrometry. The crystal structure of compound 2 has been determined by X-ray diffraction methods, and it crystallizes in the monoclinic I2/m space group. The molecular skeleton lies in the crystallographic mirror plane, in agreement with the expected theoretical planarity enforced by extended π-bonding. The crystal packing of both compounds is characterized by the R22(8) motif formed by intermolecular C–H⋯X[double bond, length as m-dash]C (X = O and S) hydrogen-bonding interactions involving the 1-benzopyran-2-one/thione moiety, as also identified by Hirshfeld surface analysis. The vibrational properties have been studied by infrared and Raman spectroscopy complemented by quantum chemical calculations and normal coordinate analysis of the potential energy distribution. The UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations, showing a clear red-shift in the HOMO–LUMO electronic transition when the chromen-2-one ring is converted into chromen-2-thione.
publishDate 2017
dc.date.none.fl_str_mv 2017-02
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/10915/101000
url http://sedici.unlp.edu.ar/handle/10915/101000
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://ri.conicet.gov.ar/11336/48645
info:eu-repo/semantics/altIdentifier/issn/1144-0546
info:eu-repo/semantics/altIdentifier/doi/10.1039/C7NJ01311F
info:eu-repo/semantics/altIdentifier/hdl/11336/48645
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
5770-5783
dc.source.none.fl_str_mv reponame:SEDICI (UNLP)
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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