Alternating behavior in furan-acetylene macrocycles reveals the size-dependency of Hückel’s rule in neutral molecules Article Swipe
Yuval Rahav
,
Shinaj K. Rajagopal
,
Or Dishi
,
Benny Bogoslavsky
,
Ori Gidron
·
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1038/s42004-023-00902-9
YOU?
·
· 2023
· Open Access
·
· DOI: https://doi.org/10.1038/s42004-023-00902-9
Aromaticity can be assigned by Hückel’s rule, which predicts that planar rings with delocalized (4 n + 2) π-electrons are aromatic, whereas those with 4 n π-electrons are antiaromatic. However, for neutral rings, the maximal value of “ n” to which Hückel’s rule applies remains unknown. Large macrocycles exhibiting global ring current can serve as models for addressing this question, but the global ring current are often overshadowed in these molecules by the local ring current of the constituent units. Here, we present a series of furan-acetylene macrocycles, ranging from the pentamer to octamer, whose neutral states display alternating contributions from global aromatic and antiaromatic ring currents. We find that the odd-membered macrocycles display global aromatic characteristics, whereas the even-membered macrocycles display contributions from globally antiaromatic ring current. These factors are expressed electronically (oxidation potentials), optically (emission spectra), and magnetically (chemical shifts), and DFT calculations predict global ring current alternations up to 54 π-electrons.
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- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1038/s42004-023-00902-9
- https://www.nature.com/articles/s42004-023-00902-9.pdf
- OA Status
- gold
- Cited By
- 9
- References
- 44
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W4378573959
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- OpenAlex ID
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https://openalex.org/W4378573959Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1038/s42004-023-00902-9Digital Object Identifier
- Title
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Alternating behavior in furan-acetylene macrocycles reveals the size-dependency of Hückel’s rule in neutral moleculesWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2023Year of publication
- Publication date
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2023-05-27Full publication date if available
- Authors
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Yuval Rahav, Shinaj K. Rajagopal, Or Dishi, Benny Bogoslavsky, Ori GidronList of authors in order
- Landing page
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https://doi.org/10.1038/s42004-023-00902-9Publisher landing page
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https://www.nature.com/articles/s42004-023-00902-9.pdfDirect link to full text PDF
- Open access
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YesWhether a free full text is available
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-
goldOpen access status per OpenAlex
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https://www.nature.com/articles/s42004-023-00902-9.pdfDirect OA link when available
- Concepts
-
Antiaromaticity, Aromaticity, Ring (chemistry), Chemistry, Delocalized electron, Furan, Computational chemistry, Ring current, Acetylene, Chemical physics, Electron, Molecule, Chemical shift, Annulene, Physics, Physical chemistry, Organic chemistry, Quantum mechanics, Magnetic field, Earth's magnetic fieldTop concepts (fields/topics) attached by OpenAlex
- Cited by
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9Total citation count in OpenAlex
- Citations by year (recent)
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2025: 7, 2024: 1, 2023: 1Per-year citation counts (last 5 years)
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44Number of works referenced by this work
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-
10Other works algorithmically related by OpenAlex
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