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dc.contributor.authorTurias, Francesc
dc.contributor.authorPoater, Jordi
dc.contributor.authorChauvin, Remi
dc.contributor.authorPoater, Albert
dc.date.accessioned2016-11-03T08:32:04Z
dc.date.available2016-11-03T08:32:04Z
dc.date.issued2015-09-25
dc.identifier.citationTurias F, Poater J, Chauvin R, Poater A (2015) How carbo-benzenes fit molecules in their inner core as do biologic ion carriers? Struct Chem 27: 249–259. Available: http://dx.doi.org/10.1007/s11224-015-0672-y.
dc.identifier.issn1040-0400
dc.identifier.issn1572-9001
dc.identifier.doi10.1007/s11224-015-0672-y
dc.identifier.urihttp://hdl.handle.net/10754/621555
dc.description.abstractThe present computational study complements experimental efforts to describe and characterize carbo-benzene derivatives as paradigms of aromatic carbo-mers. A long-lasting issue has been the possibility of the π-electron crown of the C18 carbo-benzene ring to fit metals or any chemical agents in its core. A systematic screening of candidate inclusion complexes was carried out by density functional theory calculations. Mayer bond order, aromaticity indices, and energy decomposition analyses complete the understanding of the strength of the host-guest interaction. The change in steric and electronic properties induced by the guest agent is investigated by means of steric maps. Substitution of H atoms at the carbo-benzene periphery by electron-withdrawing or electron-donating groups is shown to have a determining influence on the stability of the inclusion complex ions: while electronegative substituents enhance the recognition of cations, electropositive substituents do the same for anions. The results confirm the experimental failure hitherto to evidence a carbo-benzene complex. Nevertheless, the affinity of carbo-benzene for the potassium cation appears promising for the design of planar hydrocarbon analogues of biologic ion carriers. © 2015 Springer Science+Business Media New York.
dc.description.sponsorshipA.P. thanks the Spanish MINECO for a project CTQ2014-59832-JIN and European Commission for a Career Integration Grant (CIG09-GA-2011-293900). J. P. thanks the Netherlands Organization for Scientific Research (NWO) for financial support. The Centre National de la Recherche Scientifique (CNRS) is also acknowledged by R. C. for half a teaching sabbatical in 2014-2015. We thank the referee review that has generated an improved manuscript.
dc.publisherSpringer Nature
dc.subjectCarbo-benzene
dc.subjectDFT calculations
dc.subjectHost-guest interaction
dc.subjectInclusion complex
dc.subjectIon carrier
dc.subjectPotassium
dc.titleHow carbo-benzenes fit molecules in their inner core as do biologic ion carriers?
dc.typeArticle
dc.contributor.departmentPhysical Science and Engineering (PSE) Division
dc.identifier.journalStructural Chemistry
dc.contributor.institutionInstitut de Química Computacional i Catàlisi, Departament de Química, Universitat de Girona, Campus Montilivi, Girona, Catalonia, Spain
dc.contributor.institutionDepartment of Theoretical Chemistry, Amsterdam Centre for Multiscale Modeling (ACMM), VU University Amsterdam, De Boelelaan 1083, Amsterdam, Netherlands
dc.contributor.institutionLaboratoire de Chimie de Coordination, CNRS, 205 route de Narbonne, Toulouse Cedex 4, France
dc.contributor.institutionUPS, INPT, Université de Toulouse, Toulouse Cedex 4, France
kaust.personTurias, Francesc
kaust.personPoater, Albert
dc.date.published-online2015-09-25
dc.date.published-print2016-02


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