The close relation between cyclic delocalization, energy effects of cycles and aromaticity

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Title:The close relation between cyclic delocalization, energy effects of cycles and aromaticity
Creators:
Ponec, Robert
Fias, Stijn
Van Damme, Sofie
Bultinck, Patrick
Gutman, Ivan
Stanković, Sonja
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 74, 1, pp. 147-166
Uncontrolled Keywords:Topological resonance energy, Electron delocalization, Aromaticity, Polycyclic aromatic hydrocarbons, Chemical theory, Arenes

Abstract

New evidence questioning the multidimensionality of the aromaticity phenomenon exemplified in what is called orthogonality between the classical (structural and energetic) and magnetic aromaticity indices and measures is reported. For this purpose, the recently proposed methodologies for the quantitative characterization of the energy benefits associated with the cyclic arrangement of mobile π-electrons in polycyclic aromatic hydrocarbons are compared with the indices characterizing the extent of cyclic delocalization in the corresponding conjugated circuits. The reported close correlation between both types of indices implies that no discrepancies between classical and magnetic aromaticity measures exist provided the comparison is based on the indices of inherently local nature and/or the interfering contributions of contaminating conjugated circuits is properly taken into account in the description of aromaticity measures like topological resonance energy (TRE) or nucleus independent chemical shift (NICS).

Title:The close relation between cyclic delocalization, energy effects of cycles and aromaticity
Creators:
Ponec, Robert
Fias, Stijn
Van Damme, Sofie
Bultinck, Patrick
Gutman, Ivan
Stanković, Sonja
Uncontrolled Keywords:Topological resonance energy, Electron delocalization, Aromaticity, Polycyclic aromatic hydrocarbons, Chemical theory, Arenes
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:74
Number:1
Page Range:pp. 147-166
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc2008065UNSPECIFIED
ID Code:4092
Item Type:Article
Deposited On:02 Mar 2009 10:29
Last Modified:02 Mar 2009 09:29

Citation

Ponec, Robert; Fias, Stijn; Van Damme, Sofie; Bultinck, Patrick; Gutman, Ivan; Stanković, Sonja (2009) The close relation between cyclic delocalization, energy effects of cycles and aromaticity. Collection of Czechoslovak Chemical Communications, 74 (1). pp. 147-166. ISSN 0010-0765

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