A comparative structural analysis of arylsulfonamide chalcones with potential as a biofuel additive

• Published in: Journal of molecular structure Vol. 1276; p. 134736
• Main Authors: Vieira, Diego F., Borges, Igor D., Aguiar, Antônio S.N., Duarte, Vitor S., d'Oliveira, Giulio D.C., Vaz, Wesley F., Costa, Rogério F., Perez, Caridad N., Napolitano, Hamilton B.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15-03-2023
• Subjects: Arylsulfonamide; Biofuel; DFT; M06-2X/6-311++G(d,p); XRD; Biofuel; DFT; XRD; Arylsulfonamide; M06-2X/6-311++G(d,p)
• ISSN: 0022-2860; 1872-8014
• DOI: 10.1016/j.molstruc.2022.134736

•Arylsulfonamide chalcones show a great potential protection against oxidation of biodiesel.•Fukui functions are used to identify arylsulfonamide chalcone reactive sites.•QTAIM and NBO calculations are used to comprehensively understand supramolecular arrangements.
Biodiesel has a significant added value compared to petrodiesel regarding a series of improved properties such as biodegradability and reduction of most regulated exhaust emissions. However, some challenges associated with biodiesel include physicochemical improvements in oxidative stability, which can be addressed by antioxidants. In this aspect, chalcone derivatives are simple chemical scaffolds with industrial applications that can be boosted by the insertion of a sulfonamide group. An extensive structure characterization was carried out for arylsulfonamide chalcone N-(2-(3–4-methoxyphenyl-propanoyl)-phenyl)-benzenesulfonamide and its isomer, to describe their supramolecular arrangements and conformational changes. Solid state arrangements were described by XRD and stabilized by C–H⋯O and π⋯π stacking interactions. Theoretical calculations were carried out by DFT using the M06-2X/6-311++G(d,p) level of theory to identify the reactive sites of arylsulfonamide chalcones and their molecular electrostatic potential maps. The fundamental factors were correlated to antioxidant molecules and commercial additives found in the literature. The analysis carried out in this work will be a gateway to confirm the relationship between the structure of arylsulfonamide chalcones and their additive properties as biofuels.
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