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Magnetic Antiaromaticity─Paratropicity─Does Not Necessarily Imply Instability.

ABSTRACT: 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.

SUBMITTER: Foroutan-Nejad C

PROVIDER: S-EPMC10594649 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature

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Magnetic Antiaromaticity─Paratropicity─Does Not Necessarily Imply Instability.

Foroutan-Nejad Cina C

The Journal of organic chemistry 20230929 20

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 oft ...[more]

PMID: 37774173

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