How carbo-benzenes fit molecules in their inner core as do biologic ion carriers?

Handle URI:
http://hdl.handle.net/10754/621555
Title:
How carbo-benzenes fit molecules in their inner core as do biologic ion carriers?
Authors:
Turias, Francesc; Poater, Jordi; Chauvin, Remi; Poater, Albert ( 0000-0002-8997-2599 )
Abstract:
The 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.
KAUST Department:
Physical Sciences and Engineering (PSE) Division
Citation:
Turias 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.
Publisher:
Springer Science + Business Media
Journal:
Structural Chemistry
Issue Date:
25-Sep-2015
DOI:
10.1007/s11224-015-0672-y
Type:
Article
ISSN:
1040-0400; 1572-9001
Sponsors:
A.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.
Appears in Collections:
Articles; Physical Sciences and Engineering (PSE) Division

Full metadata record

DC FieldValue Language
dc.contributor.authorTurias, Francescen
dc.contributor.authorPoater, Jordien
dc.contributor.authorChauvin, Remien
dc.contributor.authorPoater, Alberten
dc.date.accessioned2016-11-03T08:32:04Z-
dc.date.available2016-11-03T08:32:04Z-
dc.date.issued2015-09-25en
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.en
dc.identifier.issn1040-0400en
dc.identifier.issn1572-9001en
dc.identifier.doi10.1007/s11224-015-0672-yen
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.en
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.en
dc.publisherSpringer Science + Business Mediaen
dc.subjectCarbo-benzeneen
dc.subjectDFT calculationsen
dc.subjectHost-guest interactionen
dc.subjectInclusion complexen
dc.subjectIon carrieren
dc.subjectPotassiumen
dc.titleHow carbo-benzenes fit molecules in their inner core as do biologic ion carriers?en
dc.typeArticleen
dc.contributor.departmentPhysical Sciences and Engineering (PSE) Divisionen
dc.identifier.journalStructural Chemistryen
dc.contributor.institutionInstitut de Química Computacional i Catàlisi, Departament de Química, Universitat de Girona, Campus Montilivi, Girona, Catalonia, Spainen
dc.contributor.institutionDepartment of Theoretical Chemistry, Amsterdam Centre for Multiscale Modeling (ACMM), VU University Amsterdam, De Boelelaan 1083, Amsterdam, Netherlandsen
dc.contributor.institutionLaboratoire de Chimie de Coordination, CNRS, 205 route de Narbonne, Toulouse Cedex 4, Franceen
dc.contributor.institutionUPS, INPT, Université de Toulouse, Toulouse Cedex 4, Franceen
kaust.authorTurias, Francescen
kaust.authorPoater, Alberten
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