The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -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.
Fil: Delgado Espinosa, Zuly Yuliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Mahmood, Shamsul. Quaid-I-Azam University; Pakistán
Fil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Materia
X-ray Crystal Structure
Hirshfeld analysis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/48645
Acceder
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network_name_str CONICET Digital (CONICET)
spelling The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analoguesDelgado Espinosa, Zuly YulianaSaeed, AamerMahmood, ShamsulEcheverría, Gustavo AlbertoPiro, Oscar EnriqueErben, Mauricio FedericoX-ray Crystal StructureHirshfeld analysishttps://purl.org/becyt/ford/1.3https://purl.org/becyt/ford/14,7-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.Fil: Delgado Espinosa, Zuly Yuliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaFil: Saeed, Aamer. Quaid-I-Azam University; PakistánFil: Mahmood, Shamsul. Quaid-I-Azam University; PakistánFil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; ArgentinaFil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; ArgentinaRoyal Society of Chemistry2017-02info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/48645Delgado Espinosa, Zuly Yuliana; Saeed, Aamer; Mahmood, Shamsul; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues; Royal Society of Chemistry; New Journal of Chemistry; 41; 13; 2-2017; 5770-57831144-0546CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1039/C7NJ01311Finfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/NJ/C7NJ01311Finfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-12-23T13:35:33Zoai:ri.conicet.gov.ar:11336/48645instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-12-23 13:35:33.945CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
title The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
spellingShingle The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
Delgado Espinosa, Zuly Yuliana
X-ray Crystal Structure
Hirshfeld analysis
title_short The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
title_full The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
title_fullStr The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
title_full_unstemmed The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues
title_sort The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -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 X-ray Crystal Structure
Hirshfeld analysis
topic X-ray Crystal Structure
Hirshfeld analysis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.3
https://purl.org/becyt/ford/1
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.
Fil: Delgado Espinosa, Zuly Yuliana. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
Fil: Saeed, Aamer. Quaid-I-Azam University; Pakistán
Fil: Mahmood, Shamsul. Quaid-I-Azam University; Pakistán
Fil: Echeverría, Gustavo Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Piro, Oscar Enrique. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Instituto de Física La Plata. Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Instituto de Física La Plata; Argentina
Fil: Erben, Mauricio Federico. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - La Plata. Centro de Química Inorgánica "Dr. Pedro J. Aymonino". Universidad Nacional de La Plata. Facultad de Ciencias Exactas. Centro de Química Inorgánica "Dr. Pedro J. Aymonino"; Argentina
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
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://hdl.handle.net/11336/48645
Delgado Espinosa, Zuly Yuliana; Saeed, Aamer; Mahmood, Shamsul; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues; Royal Society of Chemistry; New Journal of Chemistry; 41; 13; 2-2017; 5770-5783
1144-0546
CONICET Digital
CONICET
url http://hdl.handle.net/11336/48645
identifier_str_mv Delgado Espinosa, Zuly Yuliana; Saeed, Aamer; Mahmood, Shamsul; Echeverría, Gustavo Alberto; Piro, Oscar Enrique; et al.; The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2: H -chromen-2-one/thione analogues; Royal Society of Chemistry; New Journal of Chemistry; 41; 13; 2-2017; 5770-5783
1144-0546
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/C7NJ01311F
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2017/NJ/C7NJ01311F
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society of Chemistry
publisher.none.fl_str_mv Royal Society of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.952241

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