Estimation of Resonance Energy from Forced Nonplanar Conformations of Conjugated Molecules

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Title:Estimation of Resonance Energy from Forced Nonplanar Conformations of Conjugated Molecules
Creators:
Böhm, Stanislav
Exner, Otto
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 10, pp. 1577-1588
Uncontrolled Keywords:Isodesmic reaction, <i>Ab initio</i> calculations, Resonance energy, Inhibited conjugation, Chemometrics, DFT, Buta-1,3-diene, Dienes, Substituent effects

Abstract

Energies of 39 derivatives of buta-1,3-diene in the twisted conformation were calculated within the framework of the density functional theory at the B3LYP/6-311+G(d,p) level. By comparing with the same molecules in their natural minimum-energy conformations, a scale of resonance effects of various substituents was obtained and expressed in terms of isodesmic reactions. Comparison with other similar scales revealed that this model is not particularly advantageous, its main shortcoming being the relatively small effect. In any case it confirmed that the scales of resonance effects obtained from different models are only very roughly proportional: the classical model of resonance works well in representative examples but has its clear limitation when unduly extended. <p>

Title:Estimation of Resonance Energy from Forced Nonplanar Conformations of Conjugated Molecules
Creators:
Böhm, Stanislav
Exner, Otto
Uncontrolled Keywords:Isodesmic reaction, <i>Ab initio</i> calculations, Resonance energy, Inhibited conjugation, Chemometrics, DFT, Buta-1,3-diene, Dienes, Substituent effects
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:70
Number:10
Page Range:pp. 1577-1588
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051577UNSPECIFIED
ID Code:2426
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Böhm, Stanislav; Exner, Otto (2005) Estimation of Resonance Energy from Forced Nonplanar Conformations of Conjugated Molecules. Collection of Czechoslovak Chemical Communications, 70 (10). pp. 1577-1588. ISSN 0010-0765

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