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Cited by 41Synthesis and Properties of Aromatic CompoundsCyclization and Aryne ChemistryChemical Reactions and Mechanisms

Magnetic Antiaromaticity─Paratropicity─Does Not Necessarily Imply Instability

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Foroutan-Nejad, Cina·2023·The Journal of Organic Chemistry
DOI 10.1021/acs.joc.3c01807PMC PMC10594649
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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.

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  • Foroutan-Nejad calculated magnetically induced ring currents of benzene radical cations and anions, which were strongly paratropic (MICD = -17.3, -47.4 and 12.0 nA/T for radical cation, anion, and neutral benzene, respectively).

    “Foroutan-Nejad calculated magnetically induced ring currents of benzene radical cations and anions, which were strongly paratropic (MICD = -17.3,-47.4 and 12.0 nA/T for radical cation, anion, and neutral benzene, respectively).”

    From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [171]

  • Radical anion of 1,2-diazine has higher ISE = 11.2 kcal/mol (ISE = 34.0 kcal/mol for neutral diazine), but also sustains strong paratropic ring current.

    “Radical anion of 1,2-diazine has higher ISE = 11.2 kcal/mol (ISE = 34.0kcal/mol for neutral diazine), but also sustains strong paratropic ring current [171].”

    From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [171]

  • Both benzene radical ions are energetically stabilized and have ISE = 7.4 and 6.7 kcal/mol, respectively (ISE = 33.5 kcal/mol for benzene).

    “However, both radical ions are energetically stabilized and have ISE = 7.4 and 6.7 kcal/mol, respectively (ISE = 33.5 kcal/mol for benzene).”

    From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [171]

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Cited by

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Authors
Foroutan-Nejad, C.
Affiliations
Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland
ORCID
Foroutan-Nejad, Cina
Venue
The Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Published
2023-09-29
Volume
88
Issue
20
Pages
14831-14835
ISSN
  • 0022-3263 (ISSN-L)
  • 1520-6904
DOI
10.1021/acs.joc.3c01807
PMC
PMC10594649
OpenAlex
W4387163425
Cited by
41
References
4
Citations by year
2026: 13 · 2025: 15 · 2024: 13
FWCI
4.20
Type
journal article
Language
en
Open access
Licence
Locations
  • The Journal of Organic Chemistry (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • CeON Repository (Centre for Evaluation in Education and Science) (submittedVersion, cc-by)
Funders
Narodowe Centrum Nauki (2020/39/B/ST4/02022)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
  • Physical Sciences › Chemistry › Organic Chemistry › Cyclization and Aryne Chemistry
  • Physical Sciences › Chemistry › Physical and Theoretical Chemistry › Chemical Reactions and Mechanisms
Keywords
antiaromaticity, radical ions, cyclic conjugation, aromatic stabilization

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