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dc.contributor.authorPuttreddy, Rakesh
dc.contributor.authorBeyeh, Ngong Kodiah
dc.contributor.authorTaimoory, S. Maryamdokht
dc.contributor.authorMeister, Daniel
dc.contributor.authorTrant, John F.
dc.contributor.authorRissanen, Kari
dc.date.accessioned2018-07-17T07:48:21Z
dc.date.available2018-07-17T07:48:21Z
dc.date.issued2018
dc.identifier.citationPuttreddy, R., Beyeh, N. K., Taimoory, S. M., Meister, D., Trant, J. F., & Rissanen, K. (2018). Host-guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides : solid-state, solution and computational studies. <i>Beilstein Journal of Organic Chemistry</i>, <i>14</i>, 1723-1733. <a href="https://doi.org/10.3762/bjoc.14.146" target="_blank">https://doi.org/10.3762/bjoc.14.146</a>
dc.identifier.otherCONVID_28162407
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/58951
dc.description.abstractHost–guest complexes of C-hexyl-2-bromoresorcinarene (BrC6) with twelve potential aromatic N-oxide guests were studied using single crystal X-ray diffraction analysis and 1H NMR spectroscopy. In the solid state, of the nine obtained X-ray crystal structures, eight were consistent with the formation of BrC6-N-oxide endo complexes. The lone exception was from the association between 4-phenylpyridine N-oxide and BrC6, in that case the host forms a self-inclusion complex. BrC6, as opposed to more rigid previously studied C-ethyl-2-bromoresorcinarene and C-propyl-2-bromoresorcinarene, undergoes remarkable cavity conformational changes to host different N-oxide guests through C–H···π(host) interactions. In solution phase CD3OD/CDCl3 (1:1 v/v), all twelve N-oxide guests form endo complexes according to 1H NMR; however, in more polar CD3OD/DMSO-d6 (9:1 v/v), only three N-oxides with electron-donating groups form solution-phase endo complexes with BrC6. In solid-state studies, 3-methylpyridine N-oxide+BrC6 crystallises with both the upper- and lower-rim BrC6 cavities occupied by N-oxide guests. Computational DFT-based studies support that lower-rim long hexyl chains provide the additional stability required for this ditopic behaviour. The lower-rim cavity, far from being a neutral hydrophobic environment, is a highly polarizable electrostatically positive surface, aiding in the binding of polar guests such as N-oxides.fi
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherBeilstein-Institut zur Foerderung der Chemischen Wissenschaften
dc.relation.ispartofseriesBeilstein Journal of Organic Chemistry
dc.rightsCC BY 4.0
dc.subject.otheraromatic N-oxides
dc.subject.otherC–H···π Interactions
dc.subject.otherditopic receptors
dc.subject.otherendo/exo complexation
dc.subject.otherhost–guest chemistry
dc.subject.otherresorcinarenes
dc.titleHost-guest complexes of conformationally flexible C-hexyl-2-bromoresorcinarene and aromatic N-oxides : solid-state, solution and computational studies
dc.typeresearch article
dc.identifier.urnURN:NBN:fi:jyu-201807113514
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2018-07-11T06:15:09Z
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange1723-1733
dc.relation.issn2195-951X
dc.relation.numberinseries0
dc.relation.volume14
dc.type.versionpublishedVersion
dc.rights.copyright© 2018 Puttreddy et al.; licensee Beilstein-Institut.
dc.rights.accesslevelopenAccessfi
dc.type.publicationarticle
dc.subject.ysosupramolekulaarinen kemia
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.3762/bjoc.14.146
dc.type.okmA1


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