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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. <i>Crystals</i>, <i>7</i>(7), Article 214. <a href="https://doi.org/10.3390/cryst7070214" target="_blank">https://doi.org/10.3390/cryst7070214</a>
dc.identifier.otherCONVID_27116625
dc.identifier.otherTUTKAID_74426
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/54968
dc.description.abstractThe C-ethyl-2-methylresorcinarene (1) forms 1:1 in-cavity complexes with aromatic N,N′-dioxides, only if each of the aromatic rings has an N−O group. The structurally different C-shaped 2,2′-bipyridine N,N′-dioxide (2,2′-BiPyNO) and the linear rod-shaped 4,4′-bipyridine N,N′-dioxide (4,4′-BiPyNO) both form 1:1 in-cavity complexes with the host resorcinarene in C4v crown and C2v conformations, respectively. In the solid state, the host–guest interactions between the 1,3-bis(4-pyridyl)propane N,N′-dioxide (BiPyPNO) and the host 1 stabilize the unfavorable anti-gauche conformation. Contrary to the N,N′-dioxide guests, the mono-N-oxide guest, 4-phenylpyridine N-oxide (4PhPyNO), does not form an in-cavity complex in the solid state. The host–guest complexation and the relative guest affinities were studied through 1H NMR competition experiments in methanol. Single-crystal X-ray crystallography of the 1:1 complexes supports the proposed solution-state structures, also revealing strong hydrogen bonds between the host and the guests, not observed in solution owing to hydrogen/deuterium (H/D) exchange processes in methanol.en
dc.languageeng
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.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.oppiaineKemiafi
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineChemistryen
dc.contributor.oppiaineOrganic Chemistryen
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.numberinseries7
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.relation.grantnumber263256
dc.relation.grantnumber292746
dc.relation.grantnumber298817
dc.subject.ysoorgaaninen kemia
dc.subject.ysovetysidokset
dc.subject.ysoröntgenkristallografia
jyx.subject.urihttp://www.yso.fi/onto/yso/p11902
jyx.subject.urihttp://www.yso.fi/onto/yso/p38131
jyx.subject.urihttp://www.yso.fi/onto/yso/p29058
dc.rights.urlhttp://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3390/cryst7070214
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
dc.relation.funderAcademy of Finlanden
jyx.fundingprogramAkatemiaprofessorin tehtävä, SAfi
jyx.fundingprogramAkatemiaprofessorin tutkimuskulut, SAfi
jyx.fundingprogramTutkijatohtori, SAfi
jyx.fundingprogramResearch post as Academy Professor, AoFen
jyx.fundingprogramResearch costs of Academy Professor, AoFen
jyx.fundingprogramPostdoctoral Researcher, AoFen
jyx.fundinginformationThe authors gratefully acknowledge financial support from the Academy of Finland (R.P. grant no. 298817, K.R.: grant nos. 265328, 263256, and 292746; N.K.B.: grant no. 258653, R.H.A.R.: grant no. 272579), the University of Jyvaskyla, and Aalto University. This work was supported by the Academy of Finland through its Centres of Excellence Programme (HYBER 2014-2019).


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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.