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Structural Chemistry

, Volume 27, Issue 1, pp 249–259 | Cite as

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

  • Francesc Turias
  • Jordi Poater
  • Remi ChauvinEmail author
  • Albert PoaterEmail author
Original Research

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.

Keywords

Carbo-benzene DFT calculations Host–guest interaction Inclusion complex Ion carrier Potassium 

Notes

Acknowledgments

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.

Supplementary material

11224_2015_672_MOESM1_ESM.doc (1.1 mb)
Supplementary material 1 (DOC 1131 kb)

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Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  1. 1.Institut de Química Computacional i Catàlisi and Departament de QuímicaUniversitat de GironaGironaSpain
  2. 2.Physical Sciences and Engineering Division, Kaust Catalysis CentreKing Abdullah University of Science and TechnologyThuwalSaudi Arabia
  3. 3.Department of Theoretical Chemistry and Amsterdam Centre for Multiscale Modeling (ACMM)VU University AmsterdamAmsterdamThe Netherlands
  4. 4.Laboratoire de Chimie de CoordinationCNRSToulouse Cedex 4France
  5. 5.UPS, INPTUniversité de ToulouseToulouse Cedex 4France

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