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
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).
Showing items with similar title or keywords.
Synthesis and X-ray Crystal Structure of New Substituted 3-4′-Bipyrazole Derivatives : Hirshfeld Analysis, DFT and NBO Studies Boraei, Ahmed T. A.; Haukka, Matti; Sarhan, Ahmed A. M.; Soliman, Saied M.; Al-Majid, Abdullah Mohammed; Barakat, Assem (MDPI AG, 2021)A new compounds named 3-4′-bipyrazoles 2 and 3 were synthesized in high chemical yield from a reaction of pyran-2,4-diketone 1 with aryl hydrazines under thermal conditions in MeOH. Compound 2 was unambiguously confirmed ...
Brosge, Felix; Kochs, Johanne,s Florian; Bregu, Mariela; Truong, Khai-Nghi; Rissanen, Kari; Bolm, Carsten (American Chemical Society (ACS), 2020)At elevated temperatures, N-cyanosulfoximines react with Meldrum’s acid derivatives to give sulfoximines with N-bound 5-carbonyl-1,3-oxazine-2,4-dione groups. A representative product was characterized by single-crystal ...
Experimental and computational studies of unconventional main group compounds : stable radicals and reactive intermediates Hurmalainen, Juha (University of Jyväskylä, 2017)Ever since their discovery, radicals have intrigued the minds of experimental and theoretical chemists alike. While the vast majority of radicals are transient species, a large number of stable and persistent radicals ...
Synthesis and biological evaluation of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepine and its cycloalkane and cycloalkene condensed analogues El Haimer, Mohamed; Palkó, Márta; Haukka, Matti; Gajdács, Márió; Zupkó, István; Fülöp, Ferenc (Royal Society of Chemistry (RSC), 2021)Derivatives of the new ring system benzo[f]pyrimido[1,2-d][1,2,3]triazolo[1,5-a][1,4]diazepinone and its cycloalkane and cycloalkene condensed analogues have been conveniently synthesized through a three-step reaction ...
Ding, Xin; Tuikka, Matti; Haukka, Matti (MDPI, 2020)Sulfur is a widely used halogen bond (XB) acceptor, but only a limited number of neutral XB acceptors with bifurcated sp3-S sites have been reported. In this work a new bidentate XB acceptor, 1-(4-pyridyl)-4-thiopyridine ...