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

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

A.P. thanks the Spanish MINECO for a project CTQ2014-59832-JIN and European Commission for a Career Integration Grant (CIG09-GA-2011-293900)

Springer Verlag

Manager: Ministerio de Economía y Competitividad (Espanya)
Author: Turias, Francesc
Poater i Teixidor, Jordi
Chauvin, Remi
Poater Teixidor, Albert
Date: 2016 February
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
A.P. thanks the Spanish MINECO for a project CTQ2014-59832-JIN and European Commission for a Career Integration Grant (CIG09-GA-2011-293900)
Format: application/pdf
Document access: http://hdl.handle.net/10256/13293
Language: eng
Publisher: Springer Verlag
Collection: info:eu-repo/semantics/altIdentifier/doi/10.1007/s11224-015-0672-y
info:eu-repo/semantics/altIdentifier/issn/1040-0400
info:eu-repo/semantics/altIdentifier/eissn/1572-9001
info:eu-repo/grantAgreement/MINECO//CTQ2014-59832-JIN/ES/ESCANEO COMPUTACIONAL DE RELACIONES ESTRUCTURA%2FACTIVIDAD DE CATALIZADORES DE OXIDACION DEL AGUA PARA LA GENERACION DE H2/
info:eu-repo/grantAgreement/EC/FP7/293900/EU/Ab initio Statics and Molecular Dynamics Simulation of Olefin Metathesis Catalysts for pharmacological purposes/COMPUTEDRUG
Rights: Tots els drets reservats
Subject: Funcional de densitat, Teoria del
Density functionals
Química -- Informàtica
Chemistry -- Data processing
Title: How carbo-benzenes fit molecules in their inner core as do biologic ion carriers?
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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