Synthesis, experimental and theoretical study of novel 2-haloalkyl (-CF2H, -CCl2H, -CF2CF3)-, 3-bromo and bromomethyl substituted chromones

O, Ena G. Narváez; Bonilla, Mariel; Zurita, Daniel A.; Alcívar, D L Christian; Heredia-Moya, Jorge; Ulic, Sonia E.; Jios, Jorge L.; Piro, Oscar E.; Echeverría, Gustavo A.; Langer, Peter

doi:10.1016/j.jfluchem.2020.109717

Cited by 6 publications

(8 citation statements)

References 47 publications

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“…Particularly, the C3 -H3 A•••F2 intermolecular contact displayed an important contribution with a relative high impact of dispersive, repulsive and total energy of −23.4 kcal/mol, 12.9 kcal/mol and −21.2 kcal/mol, respectively. The interactions' energy results are in agreement with those observed in 3-dibromomethyl-2-difluoromethylchromone [5]. Moreover, shape index and curvedness properties evidence π•••π stacking and C-O•••π interactions [33], which arise from planar stacking arrangements between the chromone rings.…”

Section: Hirshfeld Surface Analysissupporting

confidence: 83%

“…The strong bands at 203 nm for 2 and 204 nm for 3-5 derive from electronic excitations from HOMO → LUMO + 5 (2) and HOMO − 2 → LUMO + 2 (3)(4)(5). The absorption at 203 nm (calc.…”

Section: Electronic Spectramentioning

confidence: 99%

“…The absorption at 204 nm (3)(4)(5) is originated in all cases from π → π* transitions within the aromatic ring and to π*-orbitals of C=C and N2=N3 bonds.…”

Section: Electronic Spectramentioning

confidence: 99%

“…Chromone derivatives with reactive functional groups such as halogens [1,2], haloalkyl [3][4][5], hydroxyl [6], amino [7,8] and azide [8,9] are important cores and precursors for pharmacologically active compounds (anti-cancer, anti-HIV, antioxidant, anti-tubercular, anti-inflammatory, analgesic, antimicrobial, anti-malaria, gastroprotective, antihistamine and antihypertensive) [10][11][12][13][14]. Among them, haloalkyl groups and azides are particularly relevant, both for their accessible synthetic routes and for their wide use as precursors of reactive species [15].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Experimental and Theoretical Study of Azidochromones

et al. 2022

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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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Section: Hirshfeld Surface Analysissupporting

confidence: 83%

“…The strong bands at 203 nm for 2 and 204 nm for 3-5 derive from electronic excitations from HOMO → LUMO + 5 (2) and HOMO − 2 → LUMO + 2 (3)(4)(5). The absorption at 203 nm (calc.…”

Section: Electronic Spectramentioning

confidence: 99%

“…The absorption at 204 nm (3)(4)(5) is originated in all cases from π → π* transitions within the aromatic ring and to π*-orbitals of C=C and N2=N3 bonds.…”

Section: Electronic Spectramentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis, Experimental and Theoretical Study of Azidochromones

et al. 2022

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“…The chromone derivatives present absorption maxima in the UV-A region, located around 300-330 nm, in agreement with the UV-Vis profile of chromones without aromatic or π-extended substituents. [25][26] The presence of an electronwithdrawing fluorine substituent slightly affects the absorption maxima, while methoxy-substituted compounds showed a redshifted absorption band of around 30 nm. Conversely, changes in solvent polarity do not interfere with the ground state of chromones.…”

Section: Photophysical Investigationsmentioning

confidence: 99%

3‐Halochromones Through Oxidative α‐Halogenation of Enaminones and its Photophysical Investigation: Another Case of Photo‐induced Partially Aromatised Intramolecular Charge Transfer?

Neto,

Coelho,

Doerner

et al. 2024

Chemistry An Asian Journal

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A versatile synthesis strategy for fluorescent 3‐halo‐4H‐chromen‐4‐one derivatives is reported. The method involves the oxidative α‐halogenation of enaminones performed by an efficient and sustainable oxidation system. The use of Oxone® in combination with KCl, KBr, or KI enables the preparation of 3‐chloro‐, 3‐bromo‐, or 3‐iodo‐4H‐chromen‐4‐one in good to excellent yields, with great functional group tolerance where the protocol is amenable to gram‐scale synthesis. The analysis of the photophysical properties of the presented 4H‐chromen‐4‐one showed absorption in the UV region and fluorescence emission in the violet‐to‐cyan region with a relatively large Stokes shift. In solution, all compounds present a dual fluorescence emission, regardless of the solvent, assigned to a partially aromatised intramolecular charge transfer mechanism, considering the presence of a pseudo‐aromatic ring in the chromone scaffold and the absence of the influence of substituent electronic features in optical behaviour.

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