Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability

[Image: see text] Magnetically induced ring currents are a conventional tool for the characterization of aromaticity. Dia- and paratropic currents are thought to be associated with stabilization (aromaticity) and destabilization (antiaromaticity), respectively. In the present work, I have questioned...

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Autor principal: Foroutan-Nejad, Cina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10594649/
https://www.ncbi.nlm.nih.gov/pubmed/37774173
http://dx.doi.org/10.1021/acs.joc.3c01807
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author Foroutan-Nejad, Cina
author_facet Foroutan-Nejad, Cina
author_sort Foroutan-Nejad, Cina
collection PubMed
description [Image: see text] Magnetically induced ring currents are a conventional tool for the characterization of aromaticity. Dia- and paratropic currents are thought to be associated with stabilization (aromaticity) and destabilization (antiaromaticity), respectively. In the present work, I have questioned the validity of the paratropic currents as a measure of antiaromaticity among monocyclic hydrocarbons. I have shown that while reduced/oxidized radical ions of hydrocarbons sustain strong paratropic currents, they often gain extra stabilization via cyclic conjugation compared to their acyclic counterparts.
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spelling pubmed-105946492023-10-25 Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability Foroutan-Nejad, Cina J Org Chem [Image: see text] Magnetically induced ring currents are a conventional tool for the characterization of aromaticity. Dia- and paratropic currents are thought to be associated with stabilization (aromaticity) and destabilization (antiaromaticity), respectively. In the present work, I have questioned the validity of the paratropic currents as a measure of antiaromaticity among monocyclic hydrocarbons. I have shown that while reduced/oxidized radical ions of hydrocarbons sustain strong paratropic currents, they often gain extra stabilization via cyclic conjugation compared to their acyclic counterparts. American Chemical Society 2023-09-29 /pmc/articles/PMC10594649/ /pubmed/37774173 http://dx.doi.org/10.1021/acs.joc.3c01807 Text en © 2023 The Author. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Foroutan-Nejad, Cina
Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability
title Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability
title_full Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability
title_fullStr Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability
title_full_unstemmed Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability
title_short Magnetic Antiaromaticity—Paratropicity—Does Not Necessarily Imply Instability
title_sort magnetic antiaromaticity—paratropicity—does not necessarily imply instability
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10594649/
https://www.ncbi.nlm.nih.gov/pubmed/37774173
http://dx.doi.org/10.1021/acs.joc.3c01807
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