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Synthesis, Experimental and Theoretical Study of Azidochromones

A series of 2-(haloalkyl)-3-azidomethyl and 6-azido chromones has been synthetized, characterized and studied by theoretical (DFT calculations) and spectroscopic methods (UV-Vis, NMR). The crystal structure of 3-azidomethyl-2-difluoromethyl chromone, determined by X-ray diffraction methods, shows a...

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Autores principales: Narváez-Ordoñez, Ena G., Pabón-Carcelén, Kevin A., Zurita-Saltos, Daniel A., Bonilla-Valladares, Pablo M., Yánez-Darquea, Trosky G., Ramos-Guerrero, Luis A., Ulic, Sonia E., Jios, Jorge L., Echeverría, Gustavo A., Piro, Oscar E., Langer, Peter, Alcívar-León, Christian D., Heredia-Moya, Jorge
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9105743/
https://www.ncbi.nlm.nih.gov/pubmed/35565987
http://dx.doi.org/10.3390/molecules27092636
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author Narváez-Ordoñez, Ena G.
Pabón-Carcelén, Kevin A.
Zurita-Saltos, Daniel A.
Bonilla-Valladares, Pablo M.
Yánez-Darquea, Trosky G.
Ramos-Guerrero, Luis A.
Ulic, Sonia E.
Jios, Jorge L.
Echeverría, Gustavo A.
Piro, Oscar E.
Langer, Peter
Alcívar-León, Christian D.
Heredia-Moya, Jorge
author_facet Narváez-Ordoñez, Ena G.
Pabón-Carcelén, Kevin A.
Zurita-Saltos, Daniel A.
Bonilla-Valladares, Pablo M.
Yánez-Darquea, Trosky G.
Ramos-Guerrero, Luis A.
Ulic, Sonia E.
Jios, Jorge L.
Echeverría, Gustavo A.
Piro, Oscar E.
Langer, Peter
Alcívar-León, Christian D.
Heredia-Moya, Jorge
author_sort Narváez-Ordoñez, Ena G.
collection PubMed
description A series of 2-(haloalkyl)-3-azidomethyl and 6-azido chromones has been synthetized, characterized and studied by theoretical (DFT calculations) and spectroscopic methods (UV-Vis, NMR). The crystal structure of 3-azidomethyl-2-difluoromethyl chromone, determined by X-ray diffraction methods, shows a planar framework due to extended π-bond delocalization. Its molecular packing is stabilized by F···H, N···H and O···H hydrogen bonds, π···π stacking and C–O···π intermolecular interactions. Moreover, AIM, NCI and Hirshfeld analysis evidenced that azido moiety has a significant role in the stabilization of crystal packing through weak intermolecular interactions, where analysis of electronic density suggested closed-shell (CS) interatomic interactions.
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spelling pubmed-91057432022-05-14 Synthesis, Experimental and Theoretical Study of Azidochromones Narváez-Ordoñez, Ena G. Pabón-Carcelén, Kevin A. Zurita-Saltos, Daniel A. Bonilla-Valladares, Pablo M. Yánez-Darquea, Trosky G. Ramos-Guerrero, Luis A. Ulic, Sonia E. Jios, Jorge L. Echeverría, Gustavo A. Piro, Oscar E. Langer, Peter Alcívar-León, Christian D. Heredia-Moya, Jorge Molecules Article A series of 2-(haloalkyl)-3-azidomethyl and 6-azido chromones has been synthetized, characterized and studied by theoretical (DFT calculations) and spectroscopic methods (UV-Vis, NMR). The crystal structure of 3-azidomethyl-2-difluoromethyl chromone, determined by X-ray diffraction methods, shows a planar framework due to extended π-bond delocalization. Its molecular packing is stabilized by F···H, N···H and O···H hydrogen bonds, π···π stacking and C–O···π intermolecular interactions. Moreover, AIM, NCI and Hirshfeld analysis evidenced that azido moiety has a significant role in the stabilization of crystal packing through weak intermolecular interactions, where analysis of electronic density suggested closed-shell (CS) interatomic interactions. MDPI 2022-04-20 /pmc/articles/PMC9105743/ /pubmed/35565987 http://dx.doi.org/10.3390/molecules27092636 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Narváez-Ordoñez, Ena G.
Pabón-Carcelén, Kevin A.
Zurita-Saltos, Daniel A.
Bonilla-Valladares, Pablo M.
Yánez-Darquea, Trosky G.
Ramos-Guerrero, Luis A.
Ulic, Sonia E.
Jios, Jorge L.
Echeverría, Gustavo A.
Piro, Oscar E.
Langer, Peter
Alcívar-León, Christian D.
Heredia-Moya, Jorge
Synthesis, Experimental and Theoretical Study of Azidochromones
title Synthesis, Experimental and Theoretical Study of Azidochromones
title_full Synthesis, Experimental and Theoretical Study of Azidochromones
title_fullStr Synthesis, Experimental and Theoretical Study of Azidochromones
title_full_unstemmed Synthesis, Experimental and Theoretical Study of Azidochromones
title_short Synthesis, Experimental and Theoretical Study of Azidochromones
title_sort synthesis, experimental and theoretical study of azidochromones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9105743/
https://www.ncbi.nlm.nih.gov/pubmed/35565987
http://dx.doi.org/10.3390/molecules27092636
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