(Anti)aromaticity of Cyclo[2 n]Carbons (n = 3–12)
Abstract
The (anti)aromaticity of the two π-systems of cyclo[2n]carbons (n = 3-12) was analyzed based on its inherent properties: molecular structure, electron delocalization, and energetic (de)stabilization. Conclusions were made based on calculated bond length and bond angle alternation (BLA and BAA), bond order (BO), energy per atom, thermodynamic stability relative to acyclic analogues, aromatic fluctuation index (FLU), electron density of delocalized bonds (EDDB), vertical resonance energy (VRE), and extra cyclic resonance energy (ECRE). It was found that rings with n = 3, 5, and 7 are doubly stabilized by aromaticity. For n = 4 and 6, the out-of-plane π-system is nearly localized with RE similar to that of acyclic analogue, but the in-plane π-system is moderately stabilized by weak delocalization. The two π-systems behave similarly starting from cyclo[16]carbon. They are nearly localized and energetically almost unaffected by (anti)aromaticity.
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C18 is non-aromatic, based on similar EDDB π values of C18 and linear C18H2 polyalkyne, similar RE per atom values for C18 and C20H2, and low ECRE values.
“However, the similar values of EDDB π of C 18 and the linear C 18 H 2 polyalkyne, together with similar RE per atom values for C 18 and C 20 H 2 , with the same number of conjugations as the cyclic molecule, and low ECRE values, led to the conclusion that C 18 is non-aromatic [68].”
From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [68]
The planar circular form of [10]annulene is stabilized by cyclic delocalization of 10 π electrons but does not exist due to large angular strain.
“It is stated that, for example, the planar circular form of [10]annulene is stabilized by cyclic delocalization of 10 π electrons, but does not exist due to the large angular strain [68].”
From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [68]
The π in of C8 is described as moderately stabilized by weak delocalization.
“As a note, the π in of C 8 is described as moderately stabilized by weak delocalization [68].”
From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [68]
The π out of C8 and both π systems of C16 are mostly localized with small negative ECRE = -11.7 kcal/mol and -10.9 kcal/mol, respectively.
“Considering that the π out of C 8 and both π systems of C 16 are mostly localized with small negative ECRE = -11.7 kcal/mol and -10.9 kcal/mol, respectively”
From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [68]
A detailed analysis characterized C16 and larger cyclo[2n]carbons as non-aromatic.
“A detailed analysis of structural, electronic, and energetic measures of (anti)aromaticity characterized C 16 and larger cyclo[2n]carbons as non-aromatic [68].”
From Aromaticity and Antiaromaticity: How to Define Them (2025) · cites this paper as [68]
Cites
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Merino, G., Solà, M., Fernández, I., Foroutan-Nejad, C., Lazzeretti, P., Frenking, G., Anderson, H. L., Sundholm, D., Cossío, F. P., Petrukhina, M. A., et al. (2023) · Chemical Science · doi:10.1039/d2sc04998h · Cited by 210 · see citing works
Cyclo[18]carbon: the smallest all-carbon electron acceptor
Stasyuk, A. J., Stasyuk, O. A., Solà, M., & Voityuk, A. A. (2020) · Chemical Communications · doi:10.1039/c9cc08399e · Cited by 128 · see citing works
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Double Aromaticity in Monocyclic Carbon, Boron, and Borocarbon Rings Based on Magnetic Criteria
Wodrich, M. D., Corminboeuf, C., Park, S. S., & Schleyer, P. V. R. (2007) · Chemistry - A European Journal · doi:10.1002/chem.200700154 · Cited by 71 · see citing works
A Short History of Cyclocarbons
Anderson, H. L., Patrick, C. W., Scriven, L. M., & Woltering, S. L. (2021) · Bulletin of the Chemical Society of Japan · doi:10.1246/bcsj.20200345 · Cited by 68 · see citing works
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Aromaticity and Antiaromaticity: How to Define Them
Baranac-Stojanović, M. (2025) · Chemistry · doi:10.3390/chemistry7040127 · Cited by 14 · see citing works
Self-citationThe (Anti)aromatic Properties of Cyclo[n]Carbons: Myth or Reality?
Stasyuk, O. A., George, G., Curutchet, C., Plasser, F., & Stasyuk, A. J. (2025) · Journal of Computational Chemistry · doi:10.1002/jcc.70283 · Cited by 2 · see citing works
“In a series of recent publications, Baranac-Stojanović analyzed various properties of even-numbered cyclo[n]carbons with n = 6–24 [30, 31].”
- Authors
- Baranac‐Stojanović, M.
- Affiliations
- University of Belgrade (RS)
- Corresponding author
- Baranac‐Stojanović, Marija
- Venue
- Chemistry – An Asian Journal
- Publisher
- Wiley
- Published
- 2025-04-09
- Volume
- 20
- Issue
- 13
- Pages
- e202500295-e202500295
- ISSN
- 1861-471X (ISSN-L)
- 1861-4728
- OpenAlex
- W4408455504
- Cited by
- 11
- References
- 6
- Citations by year
- 2026: 4 · 2025: 7
- FWCI
- 3.29
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Chemistry - An Asian Journal (publishedVersion)
- PubMed (publishedVersion)
- Cherry (Univesrity of Belgrade, Faculty of Chemistry) (submittedVersion)
- Funders
- Ministarstvo Prosvete, Nauke i Tehnološkog Razvoja (451‐03‐66/2024‐03/200168)
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and Properties of Aromatic Compounds
- Physical Sciences › Chemistry › Organic Chemistry › Cyclization and Aryne Chemistry
- Physical Sciences › Chemistry › Inorganic Chemistry › Synthesis and characterization of novel inorganic/organometallic compounds
- Keywords
- aromaticity, antiaromaticity, bond alternation, resonance energy, electron delocalization, thermodynamic stability, bond order
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