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dc.contributor.authorPamuła, Małgorzata
dc.contributor.authorBulatov, Evgeny
dc.contributor.authorHelttunen, Kaisa
dc.date.accessioned2022-10-18T09:38:45Z
dc.date.available2022-10-18T09:38:45Z
dc.date.issued2023
dc.identifier.citationPamuła, M., Bulatov, E., & Helttunen, K. (2023). Binding of ion pairs and neutral guests by aryl-extended meso‑p-hydroxyphenyl calix[4]pyrrole : The interplay between three binding sites. <i>Journal of Molecular Structure</i>, <i>1273</i>(5), Article 134268. <a href="https://doi.org/10.1016/j.molstruc.2022.134268" target="_blank">https://doi.org/10.1016/j.molstruc.2022.134268</a>
dc.identifier.otherCONVID_159126000
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/83598
dc.description.abstractAn aryl-extended calix[4]pyrrole with four meso‑p-hydroxyphenyl substituents was investigated as a host for chloride, acetate, and benzoate anions. Crystal structures of pyridinium and imidazolium chloride complexes were obtained in which chloride ions are hydrogen bonded exo-cavity to the upper rim hydroxyl groups, and the aromatic cations are bound to the shallow cavity of the host. Furthermore, the calix[4]pyrrole formed a hydrogen bonded dimeric capsule templated by inclusion of adiponitrile guest in the endo-cavity binding site. NMR titrations revealed the preference of the OH groups of the host to bind anionic guests in solution. Benzoate anion had the highest binding constant (4 700 M−1) in acetonitrile. Density functional theory (DFT) calculations indicated that the exo-cavity complex with chloride anions was favoured by 23.2 kJ/mol over the endo-cavity complex, whereas the energies of endo- and exo-cavity benzoate complexes were of similar magnitude due to dispersion interactions between the host and the guest.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherElsevier BV
dc.relation.ispartofseriesJournal of Molecular Structure
dc.rightsCC BY 4.0
dc.subject.otheranions
dc.subject.othercalix[4]pyrroles, host-guest systems
dc.subject.othersupramolecular chemistry
dc.subject.otherX-ray crystallography
dc.titleBinding of ion pairs and neutral guests by aryl-extended meso‑p-hydroxyphenyl calix[4]pyrrole : The interplay between three binding sites
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-202210184918
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen kemiafi
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineInorganic Chemistryen
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.contributor.oppiaineNanoscience Centeren
dc.contributor.oppiaineOrganic Chemistryen
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.relation.issn0022-2860
dc.relation.numberinseries5
dc.relation.volume1273
dc.type.versionpublishedVersion
dc.rights.copyright© 2022 The Author(s). Published by Elsevier B.V.
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber309910
dc.relation.grantnumber314287
dc.relation.grantnumber335685
dc.subject.ysoanionit
dc.subject.ysomolekyylit
dc.subject.ysovuorovaikutus
dc.subject.ysosupramolekulaarinen kemia
dc.subject.ysoröntgenkristallografia
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p27229
jyx.subject.urihttp://www.yso.fi/onto/yso/p2984
jyx.subject.urihttp://www.yso.fi/onto/yso/p10591
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
jyx.subject.urihttp://www.yso.fi/onto/yso/p29058
dc.rights.urlhttps://creativecommons.org/licenses/by/4.0/
dc.relation.doi10.1016/j.molstruc.2022.134268
dc.relation.funderResearch Council of Finlanden
dc.relation.funderResearch Council of Finlanden
dc.relation.funderResearch Council of Finlanden
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
jyx.fundingprogramAcademy Research Fellow, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramAkatemiatutkija, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundinginformationThis work was supported by Academy of Finland (grants 309910, 314287, 335685).
dc.type.okmA1


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