Anderson Rabello, Mayura Rubinger, Rafael Souza, Silvana Guilardi, Guilherme de Lima, Eder Tavares, Édipo Zanon, Giovanna Silva, Laércio Zambolim, Javier Ellena,
Two series of allyl sulfonamides, prepared from Morita-Baylis-Hillman adducts and primary aromatic sulfonamides, were fully characterized. The Z configuration for the products derived from 2-[hydroxy(phenyl)methyl]acrylonitrile (1) and E configuration for those derived from methyl 2-[hydroxy(phenyl)methyl]acrylate (2) were confirmed by X-ray diffraction for one compound of each series (1e, 2f). Density functional theory calculations for all allyl sulfonamides agreed with the X-ray crystallographic data. X-ray diffraction studies indicate that these compounds form dimers in their crystal structures. Fingerprint plots show that compound 1e is stabilized by H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and N⋯H/H⋯N interactions, while the compound 2f has no N⋯H/H⋯N contacts. Hirshfeld surface analyses were performed to gain insight into the behavior of these interactions. Calculated frontier orbitals showed that their highest occupied and lowest unoccupied molecular orbitals are antibonding orbitals. The allyl sulfonamides 1e and 2f are among the most active compounds in each series, inhibiting approximately 60% of the mycelial growth of Botrytis cinerea at 3 mmol L-1.
https://doi.org/10.21577/0103-5053.20210094
@article{Rabello_2021, doi = {10.21577/0103-5053.20210094}, url = {https://doi.org/10.21577%2F0103-5053.20210094}, year = 2021, publisher = {Sociedade Brasileira de Quimica ({SBQ})}, author = {Anderson Rabello and Mayura Rubinger and Rafael Souza and Silvana Guilardi and Guilherme de Lima and Eder Tavares and {\'{E}}dipo Zanon and Giovanna Silva and La{\'{e}}rcio Zambolim and Javier Ellena}, title = {Molecular Structure Studies on Allyl Sulfonamides: Synthesis, Theoretical Treatment and Evaluation of Biological Activity}, journal = {Journal of the Brazilian Chemical Society} }