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

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 t...

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Detalles Bibliográficos
Autores principales: Delgado Espinosa, Zuly Yuliana, Saeed, Aamer, Mahmood, Shamsul, Echeverría, Gustavo Alberto, Piro, Oscar Enrique, Erben, Mauricio Federico
Formato: Articulo
Lenguaje:Inglés
Publicado: 2017
Materias:
Física
Química
X-ray crystal structure
Hirshfeld analysis
Acceso en línea:http://sedici.unlp.edu.ar/handle/10915/101000
https://ri.conicet.gov.ar/11336/48645
Aporte de:
SEDICI (UNLP) de Universidad Nacional de La Plata
id I19-R120-10915-101000
record_format dspace
institution Universidad Nacional de La Plata
institution_str I-19
repository_str R-120
collection SEDICI (UNLP)
language Inglés
topic Física
Química
X-ray crystal structure
Hirshfeld analysis
spellingShingle Física
Química
X-ray crystal structure
Hirshfeld analysis
Delgado Espinosa, Zuly Yuliana
Saeed, Aamer
Mahmood, Shamsul
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Erben, Mauricio Federico
The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
topic_facet Física
Química
X-ray crystal structure
Hirshfeld analysis
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.
format Articulo
Articulo
author Delgado Espinosa, Zuly Yuliana
Saeed, Aamer
Mahmood, Shamsul
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Erben, Mauricio Federico
author_facet Delgado Espinosa, Zuly Yuliana
Saeed, Aamer
Mahmood, Shamsul
Echeverría, Gustavo Alberto
Piro, Oscar Enrique
Erben, Mauricio Federico
author_sort Delgado Espinosa, Zuly Yuliana
title The effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>H</i>-chromen-2-one/thione analogues
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 effect of chalcogen substitution on the structure and spectroscopy of 4,7-dimethyl-2<i>h</i>-chromen-2-one/thione analogues
publishDate 2017
url http://sedici.unlp.edu.ar/handle/10915/101000
https://ri.conicet.gov.ar/11336/48645
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