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Exploring the validity of the Glidewell-Lloyd extension of Clar’s π-sextet rule: assessment from polycyclic conjugated hydrocarbons

The Clar pi-sextet rule was formulated as a tool to qualitatively assign the local aromatic character of six-membered rings in benzenoid species. This simple rule has been widely validated both experimentally and theoretically. In 1984, Glidewell and Lloyd reported an extension of this rule to polycyclic conjugated hydrocarbons having rings with any even number of carbon atoms in their structure. In this work, we assess the validity of the Glidewell-Lloyd extension in 69 polycyclic conjugated hydrocarbons composed of different combinations of four-, six-, and eight-membered rings. Our results support the validity of this extension with some exceptions that are discussed. Finally, a minor modification to the rule is proposed

This work has been supported by the Ministerio de Economía y Competitividad (MINECO) of Spain (Project CTQ2014-54306-P) and the Generalitat de Catalunya (project 2014SGR931, Xarxa de Referència en Química Teòrica i Computacional, ICREA Academia 2014 prize for M.S., and grant No. 2014FI_B 00429 to O.E.B.). The EU under the FEDER grant UNGI10-4E-801 (European Fund for Regional Development) has also funded this research

© Theoretical Chemistry Accounts: Theory, Computation, and Modeling, 2015, vol. 135, núm. 8, art.205

Springer Verlag

Manager: Ministerio de Economía y Competitividad (Espanya)
Generalitat de Catalunya. Agència de Gestió d’Ajuts Universitaris i de Recerca
Author: El Bakouri, Ouissam
Poater i Teixidor, Jordi
Feixas Geronès, Ferran
Solà i Puig, Miquel
Date: 2016 August 4
Abstract: The Clar pi-sextet rule was formulated as a tool to qualitatively assign the local aromatic character of six-membered rings in benzenoid species. This simple rule has been widely validated both experimentally and theoretically. In 1984, Glidewell and Lloyd reported an extension of this rule to polycyclic conjugated hydrocarbons having rings with any even number of carbon atoms in their structure. In this work, we assess the validity of the Glidewell-Lloyd extension in 69 polycyclic conjugated hydrocarbons composed of different combinations of four-, six-, and eight-membered rings. Our results support the validity of this extension with some exceptions that are discussed. Finally, a minor modification to the rule is proposed
This work has been supported by the Ministerio de Economía y Competitividad (MINECO) of Spain (Project CTQ2014-54306-P) and the Generalitat de Catalunya (project 2014SGR931, Xarxa de Referència en Química Teòrica i Computacional, ICREA Academia 2014 prize for M.S., and grant No. 2014FI_B 00429 to O.E.B.). The EU under the FEDER grant UNGI10-4E-801 (European Fund for Regional Development) has also funded this research
Format: application/pdf
Citation: 025507
ISSN: 1432-881X (versió paper)
1432-2234 (versió electrònica)
Document access: http://hdl.handle.net/10256/12661
Language: eng
Publisher: Springer 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/10.1007/s00214-016-1970-1
Articles publicats (D-Q)
Is part of: © Theoretical Chemistry Accounts: Theory, Computation, and Modeling, 2015, vol. 135, núm. 8, art.205
Rights: Tots els drets reservats
Subject: Compostos policíclics
Polycyclic compounds
Aromaticitat (Química)
Aromaticity (Chemistry)
Compostos aromàtics
Aromatic compounds
Title: Exploring the validity of the Glidewell-Lloyd extension of Clar’s π-sextet rule: assessment from polycyclic conjugated hydrocarbons
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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