Open AccessMolecular Structure Studies on Allyl Sulfonamides: Synthesis, Theoretical Treatment and Evaluation of Biological Activity
Author(s) -
Anderson da Silva Rabello,
Mayura M. M. Rubinger,
Rafael Aparecido Carvalho Souza,
Silvana Guilardi,
Guilherme Ferreira de Lima,
Eder C. Tavares,
Édipo P Za,
Giovanna R. N Silva,
Laércio Zambolim,
Javier Ellena
Publication year - 2021
Publication title -
journal of the brazilian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.337
H-Index - 70
eISSN - 1678-4790
pISSN - 0103-5053
DOI - 10.21577/0103-5053.20210094
Subject(s) - chemistry , acrylonitrile , molecular orbital , crystallography , adduct , stereochemistry , computational chemistry , medicinal chemistry , molecule , organic chemistry , copolymer , polymer
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.