{"title":"(Anti)aromaticity of cyclo[2n]carbons (n = 3 - 12).","authors":"Marija Baranac-Stojanović","doi":"10.1002/asia.202500295","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202500295"},"PeriodicalIF":3.5000,"publicationDate":"2025-03-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202500295","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
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.
期刊介绍：
Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics.
Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews.
A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal.
Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
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