Topological Resonance Energy of Very Large Benzenoid Hydrocarbons

Abstract An approximate expression is obtained for the resonance energy of benzenoid hydrocarbons. The resonance energy is shown to depend in a simple manner on the number of six-membered cycles and on the number of Kekule structural formulae of the molecule. By this approach, the resonance energies of very large benzenoid hydrocarbons can be determined.

Download Full-text

On the Relationship between π-Electron Energy and Topological Resonance Energy

Zeitschrift für Naturforschung A ◽

10.1515/zna-2006-7-806 ◽

2006 ◽

Vol 61 (7-8) ◽

pp. 345-348

Author(s):

Ivan Gutman ◽

Slavko Radenković ◽

Nenad Trinajstić ◽

Andrej Vodopivec

Keyword(s):

Electron Energy ◽

Linear Correlation ◽

Regression Line ◽

Resonance Energy ◽

Benzenoid Hydrocarbons ◽

Good Linear ◽

The Relationship ◽

Topological Resonance Energy ◽

Good Linear Correlation

Within series of isomeric benzenoid hydrocarbons there is a very good linear correlation between the topological resonance energy (TRE) and the total π-electron energy (Eπ ). Furthermore, the slope of the TRE vs. Eπ regression line is almost independent of the benzenoid isomers considered, and (for all sets of isomers) is nearly equal to 0.5. This implies that comparison of benzenoid isomers with regard to their aromaticity can be made, with equal success, by using both TRE and Eπ . However, Eπ is computed significantly simpler than TRE, and thus advantage should be given to the former. Correlations between TRE and Eπ exist also in the case of non-benzenoid isomers (both alternant and non-alternant), but are of much inferior quality.

Download Full-text

Hueckel molecular orbital .pi. resonance energies. Benzenoid hydrocarbons

Journal of the American Chemical Society ◽

10.1021/ja00739a008 ◽

1971 ◽

Vol 93 (10) ◽

pp. 2413-2416 ◽

Cited By ~ 143

Author(s):

B. Andes Hess ◽

L. J. Schaad

Keyword(s):

Molecular Orbital ◽

Benzenoid Hydrocarbons ◽

Resonance Energies

Download Full-text

Some more difficulties with topological resonance energy

Chemical Physics Letters ◽

10.1016/0009-2614(82)83476-3 ◽

1982 ◽

Vol 85 (4) ◽

pp. 377-380 ◽

Cited By ~ 8

Author(s):

Edgar Heilbronner

Keyword(s):

Resonance Energy ◽

Topological Resonance Energy

Download Full-text

AN MMX STUDY OF BENZENE ISOMERS AND THE HYDROGENATION PRODUCTS OF BENZENE

Journal of Theoretical and Computational Chemistry ◽

10.1142/s0219633604000830 ◽

2004 ◽

Vol 03 (01) ◽

pp. 23-30 ◽

Cited By ~ 1

Author(s):

TIANMING ZUO ◽

THOMAS HUANG

Keyword(s):

Experimental Data ◽

Force Fields ◽

Resonance Energy ◽

Structure Parameters ◽

Resonance Energies

We have calculated the structures, the heats of hydrogenation and the resonance energies of benzene isomers. All structures and energies were calculated by using the MMX force fields. Using PC model, the calculated structure parameters of benzene's 8 isomers are generally in good agreements with the experimental data. The heats of hydrogenation and resonance energy of benzene isomers are parallel to those experimental data and need a systematic adjustment of 4.5 kJ/mol.

Download Full-text