Crystallographic and theoretical studies of (Z)/(E)-3-phenyl-4-(arylidene)isoxazol-5(4H)-ones

Brancatelli, Giovanna; Brunò, Giuseppe; Nicolò, Francesco; Cordaro, Massimiliano; Grassi, Giovanni; Risitano, Francesco; Scala, Angela

doi:10.1016/j.molstruc.2011.05.025

Cited by 6 publications

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References 32 publications

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“…The chemistry and the reactivity of mesoionic compounds have been extensively investigated by our research group in the last years [ 16 , 17 , 18 , 19 ], including the thermally induced addition of mesoionic (dipole) oxazolones to graphite flakes under solvent-free conditions for the direct production of a graphene sheet decorated with 2H-pyrrole derivatives ( Figure 1 , pathway d) [ 5 ].…”

Section: Introductionmentioning

confidence: 99%

“…The antibacterial activity of the new nanocomposite was assayed against selected Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli, Pseudomonas aeruginosa) bacteria. The chemistry and the reactivity of mesoionic compounds have been extensively investigated by our research group in the last years [16][17][18][19], including the thermally induced addition of mesoionic (dipole) oxazolones to graphite flakes under solvent-free conditions for the direct production of a graphene sheet decorated with 2H-pyrrole derivatives (Figure 1, pathway d) [5].…”

Section: Introductionmentioning

confidence: 99%

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Shedding Light on the Chemistry and the Properties of Münchnone Functionalized Graphene

et al. 2021

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Münchnones are mesoionic oxazolium 5-oxides with azomethine ylide characteristics that provide pyrrole derivatives by a 1,3-dipolar cycloaddition (1,3-DC) reaction with acetylenic dipolarophiles. Their reactivity was widely exploited for the synthesis of small molecules, but it was not yet investigated for the functionalization of graphene-based materials. Herein, we report our results on the preparation of münchnone functionalized graphene via cycloaddition reactions, followed by the spontaneous loss of carbon dioxide and its further chemical modification to silver/nisin nanocomposites to confer biological properties. A direct functionalization of graphite flakes into few-layers graphene decorated with pyrrole rings on the layer edge was achieved. The success of functionalization was confirmed by micro-Raman and X-ray photoelectron spectroscopies, scanning transmission electron microscopy, and thermogravimetric analysis. The 1,3-DC reactions of münchnone dipole with graphene have been investigated using density functional theory to model graphene. Finally, we explored the reactivity and the processability of münchnone functionalized graphene to produce enriched nano biomaterials endowed with antimicrobial properties.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Shedding Light on the Chemistry and the Properties of Münchnone Functionalized Graphene

et al. 2021

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Isoxazolone Reactivity Explained by Computed Electronic Structure Analysis

et al. 2019

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Summary of main observation and conclusionIsoxazol(2H)‐5‐one was chosen as a model molecule to study the structural features (α, β angles and carbonyl bond length) regarding lactone moiety in the isoxazolone species by computational calculation. DFT method with B3LYP 6‐311++G(2df,2p) basis set was used to carry out the optimization on a series (A and B families) of isoxazolones suitably substituted on double bond. The same computational method assisted by default solvent model was performed to evaluate the energies related to the tautomeric equilibrium of isoxazol(2H)‐5‐one and to the keto‐enol process (IRC). NPA (Natural Population Analysis) allowed us to understand how electron density is distributed on the heterocycle ring, highlighting reactive sites in chemical reactions and the possible interactions with biological targets.

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N-bromosuccinimide (NBS)-promoted, three-component synthesis of α,β-unsaturated isoxazol-5(4H)-ones, and spectroscopic investigation and computational study of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one

et al. 2014

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Crystallographic and theoretical studies of (Z)/(E)-3-phenyl-4-(arylidene)isoxazol-5(4H)-ones

Cited by 6 publications

References 32 publications

Shedding Light on the Chemistry and the Properties of Münchnone Functionalized Graphene

Shedding Light on the Chemistry and the Properties of Münchnone Functionalized Graphene

Isoxazolone Reactivity Explained by Computed Electronic Structure Analysis

N-bromosuccinimide (NBS)-promoted, three-component synthesis of α,β-unsaturated isoxazol-5(4H)-ones, and spectroscopic investigation and computational study of 3-methyl-4-(thiophen-2-ylmethylene)isoxazol-5(4H)-one

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