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dc.contributor.authorSchumacher, Christian
dc.contributor.authorFergen, Hannah
dc.contributor.authorPuttreddy, Rakesh
dc.contributor.authorTruong, Khai-Nghi
dc.contributor.authorRinesch, Torsten
dc.contributor.authorRissanen, Kari
dc.contributor.authorBolm, Carsten
dc.date.accessioned2020-12-22T08:47:06Z
dc.date.available2020-12-22T08:47:06Z
dc.date.issued2020
dc.identifier.citationSchumacher, 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. <i>Organic chemistry frontiers</i>, <i>7</i>(23), 3896-3906. <a href="https://doi.org/10.1039/D0QO01139H" target="_blank">https://doi.org/10.1039/D0QO01139H</a>
dc.identifier.otherCONVID_43511852
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/73382
dc.description.abstractIn 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.en
dc.format.mimetypeapplication/pdf
dc.languageeng
dc.language.isoeng
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofseriesOrganic chemistry frontiers
dc.rightsIn Copyright
dc.titleN-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202012227324
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineSoveltavan kemian yksikköfi
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineThe Unit of Applied Chemistryen
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.description.reviewstatuspeerReviewed
dc.format.pagerange3896-3906
dc.relation.issn2052-4110
dc.relation.numberinseries23
dc.relation.volume7
dc.type.versionacceptedVersion
dc.rights.copyright© 2020 Royal Society of Chemistry
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber298817
dc.subject.ysoorgaaniset yhdisteet
dc.subject.ysoröntgenkristallografia
dc.subject.ysorikkiyhdisteet
dc.subject.ysokemiallinen synteesi
dc.subject.ysokemialliset sidokset
dc.subject.ysotyppiyhdisteet
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p3841
jyx.subject.urihttp://www.yso.fi/onto/yso/p29058
jyx.subject.urihttp://www.yso.fi/onto/yso/p5731
jyx.subject.urihttp://www.yso.fi/onto/yso/p8468
jyx.subject.urihttp://www.yso.fi/onto/yso/p10130
jyx.subject.urihttp://www.yso.fi/onto/yso/p640
dc.rights.urlhttp://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.doi10.1039/D0QO01139H
dc.relation.funderSuomen Akatemiafi
dc.relation.funderAcademy of Finlanden
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundinginformationThe research work was funded by the Academy of Finland (RP: grant no. 298817).


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