Synthesis, Experimental and Theoretical Study of Azidochromones

Ena G. Narváez-Ordoñez; Kevin A. Pabón-Carcelén; Daniel A. Zurita; Pablo M. Bonilla-Valladares; Trosky G. Yánez-Darquea; Luis A. Ramos-Guerrero; Sonia E. Ulic; Jorge L. Jios; Gustavo A. Echeverría; Oscar E. Piro; Peter Langer; Christian D. Alcívar-León; HEREDIA MOYA, JORGE HUMBERTO

doi:10.3390/molecules27092636

Synthesis, Experimental and Theoretical Study of Azidochromones

Journal

Molecules

ISSN

1420-3049

Date Issued

2022-04-20

Author(s)

Ena G. Narváez-Ordoñez

Kevin A. Pabón-Carcelén

Daniel A. Zurita

Pablo M. Bonilla-Valladares

Trosky G. Yánez-Darquea

Luis A. Ramos-Guerrero

Universidad UTE

Sonia E. Ulic

Jorge L. Jios

Gustavo A. Echeverría

Oscar E. Piro

Peter Langer

Christian D. Alcívar-León

HEREDIA MOYA, JORGE HUMBERTO

Facultad de Ciencias de la Salud Eugenio Espejo

DOI

10.3390/molecules27092636

URL

https://cris.ute.edu.ec/handle/123456789/424

Abstract

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.