Item


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

Springer Verlag

Author: El Bakouri, Ouissam
Poater i Teixidor, Jordi
Feixas Geronès, Ferran
Solà i Puig, Miquel
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
Document access: http://hdl.handle.net/2072/266700
Language: eng
Publisher: Springer Verlag
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: Recercat

Subjects

Authors