Evaluation of triplet aromaticity by the indene-isoindene isomerization stabilization energy method. An, K & Zhu, J European Journal of Organic Chemistry, 2014(13):2764–2769, 2014. Publisher: WILEY-VCH Verlag ISBN: 1434-193xdoi abstract bibtex Aromaticity, one of the most important concepts in chemistry, has attracted considerable interest from both experimentalists and theoreticians. According to Baird's rule, triplet annulenes with 4n electrons are aromatic. However, the approach to evaluate the magnitude of the triplet aromaticity is less developed. Herein we apply the indene-isoindene isomerization stabilization energy (ISE) method to evaluate the aromaticity in the triplet state. The reliability of this approach can be demonstrated by the strong correlation of these indene-isoindene ISE values with nucleus-independent chemical shifts [NICS(1)(zz)] as well as methyl-methylene ISE values. Large [4n]annulenes have the tendency to be planar to achieve aromaticity in the T-1 state. Steric effects play an important role in the stabilities of large [4n]annulene isomers.
@article{an_evaluation_2014,
title = {Evaluation of triplet aromaticity by the indene-isoindene isomerization stabilization energy method},
volume = {2014},
doi = {10.1002/ejoc.201301810},
abstract = {Aromaticity, one of the most important concepts in chemistry, has attracted considerable interest from both experimentalists and theoreticians. According to Baird's rule, triplet annulenes with 4n electrons are aromatic. However, the approach to evaluate the magnitude of the triplet aromaticity is less developed. Herein we apply the indene-isoindene isomerization stabilization energy (ISE) method to evaluate the aromaticity in the triplet state. The reliability of this approach can be demonstrated by the strong correlation of these indene-isoindene ISE values with nucleus-independent chemical shifts [NICS(1)(zz)] as well as methyl-methylene ISE values. Large [4n]annulenes have the tendency to be planar to achieve aromaticity in the T-1 state. Steric effects play an important role in the stabilities of large [4n]annulene isomers.},
language = {English},
number = {13},
journal = {European Journal of Organic Chemistry},
author = {An, K and Zhu, J},
year = {2014},
note = {Publisher: WILEY-VCH Verlag
ISBN: 1434-193x},
keywords = {antiaromaticity, aromaticity, cyclobutadiene, delocalization, density functional calculations, electron localization function, excited-state aromaticity, hydrocarbons, independent chemical-shifts, macrocycles, organic-photochemistry, pi-contribution, ring currents, ring strain, triplet aromaticity},
pages = {2764--2769},
}
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