dc.contributor.author | Schumacher, Christian | |
dc.contributor.author | Fergen, Hannah | |
dc.contributor.author | Puttreddy, Rakesh | |
dc.contributor.author | Truong, Khai-Nghi | |
dc.contributor.author | Rinesch, Torsten | |
dc.contributor.author | Rissanen, Kari | |
dc.contributor.author | Bolm, Carsten | |
dc.date.accessioned | 2020-12-22T08:47:06Z | |
dc.date.available | 2020-12-22T08:47:06Z | |
dc.date.issued | 2020 | |
dc.identifier.citation | 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. <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.other | CONVID_43511852 | |
dc.identifier.uri | https://jyx.jyu.fi/handle/123456789/73382 | |
dc.description.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. | en |
dc.format.mimetype | application/pdf | |
dc.language | eng | |
dc.language.iso | eng | |
dc.publisher | Royal Society of Chemistry | |
dc.relation.ispartofseries | Organic chemistry frontiers | |
dc.rights | In Copyright | |
dc.title | N-(2,3,5,6-Tetrafluoropyridyl)sulfoximines : synthesis, X-ray crystallography, and halogen bonding | |
dc.type | article | |
dc.identifier.urn | URN:NBN:fi:jyu-202012227324 | |
dc.contributor.laitos | Kemian laitos | fi |
dc.contributor.laitos | Department of Chemistry | en |
dc.contributor.oppiaine | Soveltavan kemian yksikkö | fi |
dc.contributor.oppiaine | Orgaaninen kemia | fi |
dc.contributor.oppiaine | The Unit of Applied Chemistry | en |
dc.contributor.oppiaine | Organic Chemistry | en |
dc.type.uri | http://purl.org/eprint/type/JournalArticle | |
dc.type.coar | http://purl.org/coar/resource_type/c_2df8fbb1 | |
dc.description.reviewstatus | peerReviewed | |
dc.format.pagerange | 3896-3906 | |
dc.relation.issn | 2052-4110 | |
dc.relation.numberinseries | 23 | |
dc.relation.volume | 7 | |
dc.type.version | acceptedVersion | |
dc.rights.copyright | © 2020 Royal Society of Chemistry | |
dc.rights.accesslevel | openAccess | fi |
dc.relation.grantnumber | 298817 | |
dc.subject.yso | orgaaniset yhdisteet | |
dc.subject.yso | röntgenkristallografia | |
dc.subject.yso | rikkiyhdisteet | |
dc.subject.yso | kemiallinen synteesi | |
dc.subject.yso | kemialliset sidokset | |
dc.subject.yso | typpiyhdisteet | |
dc.format.content | fulltext | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p3841 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p29058 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p5731 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p8468 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p10130 | |
jyx.subject.uri | http://www.yso.fi/onto/yso/p640 | |
dc.rights.url | http://rightsstatements.org/page/InC/1.0/?language=en | |
dc.relation.doi | 10.1039/D0QO01139H | |
dc.relation.funder | Research Council of Finland | en |
dc.relation.funder | Suomen Akatemia | fi |
jyx.fundingprogram | Postdoctoral Researcher, AoF | en |
jyx.fundingprogram | Tutkijatohtori, SA | fi |
jyx.fundinginformation | The research work was funded by the Academy of Finland (RP: grant no. 298817). | |
dc.type.okm | A1 | |