A1 Journal article (refereed)
N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding (2020)


Schumacher, Christian; Fergen, Hannah; Puttreddy, Rakesh; Truong, Khai-Nghi; Rinesch, Torsten; Rissanen, Kari; Bolm, Carsten (2020). N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding. Organic chemistry frontiers, 7 (23), 3896-3906. DOI: 10.1039/D0QO01139H


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Publication details

All authors or editors: Schumacher, Christian; Fergen, Hannah; Puttreddy, Rakesh; Truong, Khai-Nghi; Rinesch, Torsten; Rissanen, Kari; Bolm, Carsten

Journal or series: Organic chemistry frontiers

ISSN: 2052-4110

eISSN: 2052-4129

Publication year: 2020

Volume: 7

Issue number: 23

Pages range: 3896-3906

Publisher: Royal Society of Chemistry

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/D0QO01139H

Open Access: Publication channel is not openly available

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/73382


Abstract

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.


Keywords: organic compounds; sulphur compounds; nitrogen compounds; chemical synthesis; chemical bonds; x-ray crystallography


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Last updated on 2020-22-12 at 10:47