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dc.contributor.authorHelttunen, Kaisa
dc.contributor.authorAnnala, Riia
dc.contributor.authorSuhonen, Aku
dc.contributor.authorIloniemi, Juho
dc.contributor.authorKalenius, Elina
dc.contributor.authorAragay, Gemma
dc.contributor.authorBallester, Pablo
dc.contributor.authorTuononen, Heikki
dc.contributor.authorNissinen, Maija
dc.date.accessioned2019-04-05T07:16:38Z
dc.date.available2020-03-01T22:35:28Z
dc.date.issued2019
dc.identifier.citationHelttunen, K., Annala, R., Suhonen, A., Iloniemi, J., Kalenius, E., Aragay, G., Ballester, P., Tuononen, H., & Nissinen, M. (2019). Oligoamide Foldamers as Helical Chloride Receptors : the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions. <i>Chemistry : An Asian Journal</i>, <i>14</i>(5), 647-654. <a href="https://doi.org/10.1002/asia.201801869" target="_blank">https://doi.org/10.1002/asia.201801869</a>
dc.identifier.otherCONVID_28870612
dc.identifier.otherTUTKAID_80374
dc.identifier.urihttps://jyx.jyu.fi/handle/123456789/63409
dc.description.abstractThe anion‐binding properties of three closely related oligoamide foldamers were studied using NMR spectroscopy, isothermal titration calorimetry and mass spectrometry, as well as DFT calculations. The 1H NMR spectra of the foldamers in [D6]acetone solution revealed partial preorganization by intramolecular hydrogen bonding, which creates a suitable cavity for anion binding. The limited size of the cavity, however, enabled efficient binding by the inner amide protons only for the chloride anion resulting in the formation of a thermodynamically stable 1:1 complex. All 1:1 chloride complexes displayed a significant favourable contribution of the entropy term. Most likely, this is due to the release of ordered solvent molecules solvating the free foldamer and the anion to the bulk solution upon complex formation. The introduction of electron‐withdrawing substituents in foldamers 2 and 3 had only a slight effect on the thermodynamic constants for chloride binding compared to the parent receptor. Remarkably, the binding of chloride to foldamer 3 not only produced the expected 1:1 complex but also open aggregates with 1:2 (host:anion) stoichiometry.en
dc.format.mimetypeapplication/pdf
dc.language.isoeng
dc.publisherWiley - VCH Verlag GmbH & Co. KGaA
dc.relation.ispartofseriesChemistry : An Asian Journal
dc.rightsIn Copyright
dc.subject.otherreceptors
dc.subject.otherhost-guest systems
dc.subject.otherfoldamers
dc.titleOligoamide Foldamers as Helical Chloride Receptors : the Influence of Electron-Withdrawing Substituents on Anion-Binding Interactions
dc.typearticle
dc.identifier.urnURN:NBN:fi:jyu-201903201913
dc.contributor.laitosKemian laitosfi
dc.contributor.laitosDepartment of Chemistryen
dc.contributor.oppiaineEpäorgaaninen ja analyyttinen kemiafi
dc.contributor.oppiaineOrgaaninen kemiafi
dc.contributor.oppiaineNanoscience Centerfi
dc.contributor.oppiaineInorganic and Analytical Chemistryen
dc.contributor.oppiaineOrganic Chemistryen
dc.contributor.oppiaineNanoscience Centeren
dc.type.urihttp://purl.org/eprint/type/JournalArticle
dc.date.updated2019-03-20T10:15:09Z
dc.type.coarhttp://purl.org/coar/resource_type/c_2df8fbb1
dc.description.reviewstatuspeerReviewed
dc.format.pagerange647-654
dc.relation.issn1861-4728
dc.relation.numberinseries5
dc.relation.volume14
dc.type.versionacceptedVersion
dc.rights.copyright© 2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
dc.rights.accesslevelopenAccessfi
dc.relation.grantnumber312514
dc.relation.grantnumber278743
dc.relation.grantnumber284562
dc.subject.ysoanionit
dc.subject.ysosupramolekulaarinen kemia
dc.format.contentfulltext
jyx.subject.urihttp://www.yso.fi/onto/yso/p27229
jyx.subject.urihttp://www.yso.fi/onto/yso/p37759
dc.rights.urlhttp://rightsstatements.org/page/InC/1.0/?language=en
dc.relation.doi10.1002/asia.201801869
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderSuomen Akatemiafi
dc.relation.funderResearch Council of Finlanden
dc.relation.funderResearch Council of Finlanden
dc.relation.funderResearch Council of Finlanden
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramAkatemiatutkija, SAfi
jyx.fundingprogramAkatemiatutkijan tutkimuskulut, SAfi
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundingprogramAcademy Research Fellow, AoFen
jyx.fundingprogramResearch costs of Academy Research Fellow, AoFen
jyx.fundinginformationFunding from Academy of Finland (projects 257246, 284562, 278743 and 312514) and University of Jyvaskyla (mobility funding for KH) are acknowledged. M.Sc. Esa Haapaniemi is gratefully acknowledged for assistance with the NMR measurements and Minna Kortelainen and Anniina Aho for providing foldamer 2.
dc.type.okmA1


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