Patterns of π-electron delocalization in aromatic and antiaromatic organic compounds in the light of Hückel's 4n + 2 rule

Ferran Feixas; Eduard Matito; Miquel Solà; Jordi Poater

doi:10.1039/B924972A

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Patterns of π-electron delocalization in aromatic and antiaromatic organic compounds in the light of Hückel's 4n + 2 rule†

Ferran Feixas,^a Eduard Matito,^b Miquel Solà*^a and Jordi Poater*^a

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* Corresponding authors

^a Institut de Química Computacional and Departament de Química, Universitat de Girona, Campus de Montilivi, 17071 Girona, Catalonia, Spain
E-mail: miquel.sola@udg.edu, jordi.poater@udg.edu
Fax: +34-972-418356
Tel: +34-972-418912

^b Institute of Physics, University of Szczecin, 70-451 Szczecin, Poland

Abstract

The total π-electron delocalization of a series of classical aromatic and antiaromatic organic compounds is separated into ortho (1,2), meta (1,3), para (1,4), and successive contributions (the so-called delocalization crossed terms) and the changes that take place in these crossed terms when two electrons are added or removed are analyzed. Our results show that these changes follow a similar alternation pattern in all cases. The patterns found represent a kind of electronic footprints that makes it possible to discern between aromatic and antiaromatic systems.

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Supplementary files

The supplementary information contains sections S1: effect of geometry and electronic relaxation; S2: effect of planarity restriction; Fig. S3: evolution of N + 2 for systems in Fig. 5; S4: monocycles not included in Fig. 5; Tables S5 and S6: evolution of crossed terms and aromaticity criteria at singlet and triplet states of a series of monocycles; S7: aromaticity analysis of the systems under study. PDF (2639K)

Article information

DOI: https://doi.org/10.1039/B924972A
Article type: Paper
Submitted: 26 Nov 2009
Accepted: 08 Mar 2010
First published: 18 May 2010

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Phys. Chem. Chem. Phys., 2010,12, 7126-7137

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Patterns of π-electron delocalization in aromatic and antiaromatic organic compounds in the light of Hückel's 4n + 2 rule

F. Feixas, E. Matito, M. Solà and J. Poater, Phys. Chem. Chem. Phys., 2010, 12, 7126 DOI: 10.1039/B924972A

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Physical Chemistry Chemical Physics

Patterns of π-electron delocalization in aromatic and antiaromatic organic compounds in the light of Hückel's 4n + 2 rule†

Abstract

Supplementary files

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Patterns of π-electron delocalization in aromatic and antiaromatic organic compounds in the light of Hückel's 4n + 2 rule

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