ArticleNature chemistry2023
Rupturing aromaticity by periphery overcrowding.
Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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Who cites it
9 citing papers in PubMed, 33 citations in OpenAlex.
- Excited-State Antiaromaticity in Nonbenzenoid Aromatics: Examining the Dynamics of Intramolecular Proton Transfer With a Small Driving Force.Angewandte Chemie (International ed. in English) · 2026Article
- Fluorescence mapping of atropisomer populations enabled by through-space conjugation.Nature communications · 2026Article
- Synthesis and Persistence Length Study of Defect-Free and Non-Aggregated Conjugated Ladder Polymers.JACS Au · 2025Article
- Room temperature natural light promoted DMSO/OMolecular diversity · 2025Article
- Heptannulated Perylene Diimides: Formation and Reactivity of Electron-Deficient Tropylium Cations and Heptafulvenes.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis and characterization of fluorenone derivatives with electrical properties explored using density functional theory (DFT).Scientific reports · 2024Article
- Connecting chemical worlds for a sustainable future.Chemical science · 2024Review
- Aromaticity Reversal Induced by Vibrations in Cyclo[16]carbon.Journal of the American Chemical Society · 2023Article
- Synthesis of metalla-dual-azulenes with fluoride ion recognition properties.Nature communications · 2023Article
Corrections and comments
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Authors and funding
9 authors at 2 institutions in 1 country.
Funding
Abstract
The balance between strain relief and aromatic stabilization dictates the form and function of non-planar π-aromatics. Overcrowded systems are known to undergo geometric deformations, but the energetically favourable π-electron delocalization of their aromatic ring(s) is typically preserved. In this study we incremented the strain energy of an aromatic system beyond its aromatic stabilization energy, causing it to rearrange and its aromaticity to be ruptured. We noted that increasing the steric bulk around the periphery of π-extended tropylium rings leads them to deviate from planarity to form contorted conformations in which aromatic stabilization and strain are close in energy. Under increasing strain, the aromatic π-electron delocalization of the system is broken, leading to the formation of a non-aromatic, bicyclic analogue referred to as 'Dewar tropylium'. The aromatic and non-aromatic isomers have been found to exist in rapid equilibrium with one another. This investigation demarcates the extent of steric deformation tolerated by an aromatic carbocycle and thus provides direct experimental insights into the fundamental nature of aromaticity.
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What OpenQuestion holds
Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.