N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding
Schumacher, C., Fergen, H., Puttreddy, R., Truong, K.-N., Rinesch, T., Rissanen, K., & Bolm, C. (2020). N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding. Organic chemistry frontiers, 7(23), 3896-3906. https://doi.org/10.1039/D0QO01139H
Published inOrganic chemistry frontiers
© 2020 Royal Society of Chemistry
In the presence of KOH, NH-sulfoximines react with pentafluoropyridine to give N-(tetrafluoropyridyl)sulfoximines (NTFP-sulfoximines) in moderate to excellent yields. Either a solution-based or a superior solvent-free mechanochemical protocol can be followed. X-Ray diffraction analyses of 26 products provided insight into the bond parameters and conformational rigidity of the molecular scaffold. In solid-state structures, sulfoximines with halo substituents on the S-bound arene are intermolecularly linked by C–X⋯O[double bond, length as m-dash]S (X = Cl, Br) halogen bonds. Hirshfeld surface analysis is used to assess the type of non-covalent contacts present in molecules. For mixtures of three different S-pyridyl-substituted NTFP-sulfoximines and N-iodosuccinimide (NIS) in CDCl3, association constants were determined by 1H NMR spectroscopy. The data revealed a dependence of the halogen bond strength on the position of the pyridyl nitrogen indicating the presence of N–I⋯N(S-pyridyl) interactions. Neither the S[double bond, length as m-dash]O oxygen nor the tetrafluoropyridyl-substituted nitrogen of the sulfoximine appeared to be involved in halogen bonding. ...
PublisherRoyal Society of Chemistry
ISSN Search the Publication Forum2052-4110
Publication in research information system
MetadataShow full item record
Related funder(s)Academy of Finland
Funding program(s)Postdoctoral Researcher, AoF
Additional information about fundingThe research work was funded by the Academy of Finland (RP: grant no. 298817).
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