Synthesis, Experimental and Theoretical Study of Azidochromones

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 9; p. 2636
• Main Authors: 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
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 20.04.2022; MDPI
• Subjects: Azide; azidochromone; Carbon; Chemical bonds; Crystal structure; Density Functional Theory; Fluorine; Hirshfeld surface analysis; Hydrocarbons; Hydrogen Bonding; Hydrogen bonds; Magnetic Resonance Spectroscopy; Models, Molecular; NMR; Nuclear magnetic resonance; quantum chemical calculations; spectroscopic properties; structural X-ray diffraction; X-Ray Diffraction; quantum chemical calculations; structural X-ray diffraction; Hirshfeld surface analysis; azidochromone; spectroscopic properties
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27092636

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.