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Understanding the Reactivity of Planar Polycyclic Aromatic Hydrocarbons: Towards the Graphene Limit

The Diels-Alder reactivity of maleic anhydride to the bay regions of planar polycyclic aromatic hydrocarbons has been explored computationally within the Density Functional Theory framework. It is found that the process becomes more and more exothermic and the associated activation barriers become lower and lower when the size of the system increases. This enhanced reactivity follows an exponential behavior reaching its maximum for systems having 18-20 benzenoid rings in their structures. This peculiar behavior has been analyzed in detail using the activation strain model of reactivity in combination with the energy decomposition analysis method. In addition, the influence of the change in the aromaticity strength of the polycyclic compound during the process on the respective activation barriers has been also studied

© Chemistry-A European Journal, 2016, vol. 22, núm. 30, p. 10572-10580

Wiley-VCH Verlag

Manager: Generalitat de Catalunya. Agència de Gestió d’Ajuts Universitaris i de Recerca
Ministerio de Economía y Competitividad (Espanya)
Author: García-Rodeja, Yago
Solà i Puig, Miquel
Fenández López, Israel
Date: 2016 July 18
Abstract: The Diels-Alder reactivity of maleic anhydride to the bay regions of planar polycyclic aromatic hydrocarbons has been explored computationally within the Density Functional Theory framework. It is found that the process becomes more and more exothermic and the associated activation barriers become lower and lower when the size of the system increases. This enhanced reactivity follows an exponential behavior reaching its maximum for systems having 18-20 benzenoid rings in their structures. This peculiar behavior has been analyzed in detail using the activation strain model of reactivity in combination with the energy decomposition analysis method. In addition, the influence of the change in the aromaticity strength of the polycyclic compound during the process on the respective activation barriers has been also studied
Format: application/pdf
Citation: 025384
ISSN: 0947-6539 (versió paper)
1521-3765 (versió electrònica)
Document access: http://hdl.handle.net/10256/12628
Language: eng
Publisher: Wiley-VCH Verlag
Collection: MINECO/PE 2015-2017/CTQ2014-54306-P
AGAUR/2014-2016/2014 SGR-931
Versió postprint del document publicat a: http://dx.doi.org/10.1002/chem.201600900
Articles publicats (D-Q)
Is part of: © Chemistry-A European Journal, 2016, vol. 22, núm. 30, p. 10572-10580
Rights: Tots els drets reservats
Subject: Compostos policíclics
Polycyclic compounds
Reactivitat (Química)
Reactivity (Chemistry)
Funcional de densitat, Teoria del
Density functionals
Diels-Alder, Reacció de
Diels-Alder reaction
Title: Understanding the Reactivity of Planar Polycyclic Aromatic Hydrocarbons: Towards the Graphene Limit
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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