Croatica Chemica Acta, Vol. 94 No. 4, 2021.
Original scientific paper
https://doi.org/10.5562/cca3888
Competition Between Sextet Aromaticity and Cyclobutadiene Antiaromaticity within the Same Molecule: Location is Important
Jerry Ray Dias
orcid.org/0000-0001-7772-4283
; Department of Chemistry, University of Missouri, Kansas City, MO 64110-2499, USA
Abstract
The interplay between aromaticity and antiaromaticity is maximized in [n]phenylenes. In their smaller isomer sets, some isomers can be aromatic while others can be antiaromatic. The sum of the superimposed constituent circuits contributes to the individual ring aromaticity. Both cyclic conjugated energy (CCEi = efi ) of Bosanac and Gutman and Aihara’s topological bond resonance energy (t-BRE) are good measures of relative degree of ring aromatic/antiaromatic character. Topological resonance energy (TRE) is a reliable measure of global molecular aromaticity/antiaromaticity because it is independent of selection of frame-of-reference molecules for calibration.
Keywords
ring resonance energy; topological resonance energy; aromaticity/antiaromaticity; [n]phenylenes
Hrčak ID:
281365
URI
Publication date:
8.8.2022.
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