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dc.contributor.authorPuttreddy, Rakesh
dc.contributor.authorTopic, Filip
dc.contributor.authorValkonen, Arto
dc.contributor.authorRissanen, Kari
dc.date.accessioned2017-08-01T12:08:24Z
dc.date.available2017-08-01T12:08:24Z
dc.date.issued2017
dc.identifier.citationPuttreddy, R., Topic, F., Valkonen, A., & Rissanen, K. (2017). Halogen-Bonded Co-Crystals of Aromatic N-oxides : Polydentate Acceptors for Halogen and Hydrogen Bonds. <em>Crystals</em>, 7 (7), 214. <a href="https://doi.org/10.3390/cryst7070214">doi:10.3390/cryst7070214</a>
dc.identifier.otherTUTKAID_74426
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/54968
dc.description.abstractSeventeen new halogen-bonded co-crystals characterized by single crystal X-ray analysis are presented from 8 × 4 combinations using methyl-substituted pyridine N-oxides and 1,ω-diiodoperfluoroalkanes. The N−O group in six of 17 co-crystals is monodentate and 11 have μ-O,O bidentate halogen bond acceptor modes. Remarkably, the N−O group in co-crystals of 3-methyl-, 4-methyl- and 3,4-dimethylpyridineN-oxides with octafluoro-1,4-diiodobutane acted as a μ-O,O,O,O halogen and hydrogen bond acceptor, while acting as a μ-O,O,O acceptor in the co-crystal of 2,5-dimethylpyridineN-oxide and tetrafluoro-1,2-diiodoethane. The C−H···O−N hydrogen bonds demonstrated the polydentate cooperativity of the N−O group as a mixed halogen-hydrogen bond acceptor. The co-crystal of 2,4,6-trimethylpyridineN-oxide and dodecafluoro-1,6-diiodohexane exhibited C−I···O−−N+ halogen bonds with RXB value 0.76, the shortest of its kind compared to previously reported structures. The RXB values between 0.76 and 0.83 suggested that the C−I···O−−N halogen bonds are moderately strong compared to our previously studied N−−I···O−−N system, with RXB in the order 0.66.
dc.language.isoeng
dc.publisherMDPI AG
dc.relation.ispartofseriesCrystals
dc.relation.urihttp://www.mdpi.com/2073-4352/7/7/214
dc.subject.otherhalogen bond
dc.subject.otherhydrogen bond
dc.subject.otheraromatic N-oxides
dc.subject.otherperfluoroalkyl
dc.subject.otherdiiodoperfluoroalkanes
dc.subject.otherpolydentate
dc.subject.otherN−O group
dc.subject.othercooperativity
dc.subject.otherC−
dc.subject.otherH···O interactions
dc.titleHalogen-Bonded Co-Crystals of Aromatic N-oxides : Polydentate Acceptors for Halogen and Hydrogen Bonds
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201707173303
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineKemia
dc.contributor.oppiaineOrgaaninen kemia
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2017-07-17T06:15:12Z
dc.type.coarjournal article
dc.description.reviewstatuspeerReviewed
dc.relation.issn2073-4352
dc.relation.volume7
dc.type.versionpublishedVersion
dc.rights.copyright© 2017 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
dc.rights.accesslevelopenAccessfi
dc.rights.urlhttp://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3390/cryst7070214


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© 2017 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
Except where otherwise noted, this item's license is described as © 2017 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.