ArticleACS omega2021
Fluoromaticity: The Molecular Orbital Contributions of Fluorine Substituents to the π-Systems of Aromatic Rings.
Article in ACS omega, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Molecular engineering of bistetrafluoropyridine aryl ethers: a general platform for stable and programmable amorphous organic solids.RSC advances · 2026Article
- How fluorine substituents strengthen aryl C-H bonds.Chemical science · 2026Article
- Metabolic Stability of Fluorinated Small Molecules: A Physical Organic Chemistry Perspective.Journal of medicinal chemistry · 2026Review
- Get a better glimpse on sequential photoreactions of trisnorbornadienes withBeilstein journal of organic chemistry · 2026Article
- A novel sulfonamide derivative suppresses gastrointestinal cancer progression by targeting Axin2 and β-catenin.Scientific reports · 2025Article
- Direct detection of an NH-π hydrogen bond in an intrinsically disordered peptide.Nature communications · 2025Article
- Tizoxanide associated with anti-virulent activity controls fire blight disease caused by Erwinia amylovora in Malus asiatica.Communications biology · 2025Article
- Investigating the Site-Specific Impact of Fluorine Substitution on Aromatic Interactions in a Tryptophan Zipper Peptide.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Planarity Is Not Plain: Closed- vs Open-Shell Reactivity of a Structurally Constrained, Doubly Reduced Arylborane toward Fluorobenzenes.Journal of the American Chemical Society · 2025Article
- The Geometry and Nature of C─I···O─N Interactions in Perfluoroiodobenzene-Pyridine N-oxide Halogen-Bonded Complexes.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2024Article
- Conformational Analysis of 1,5-Diaryl-3-Oxo-1,4-Pentadiene Derivatives: A Nuclear Overhauser Effect Spectroscopy Investigation.International journal of molecular sciences · 2023Article
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Authors and funding
3 authors.
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Abstract
The addition of fluorine atoms to an aromatic ring brings about an additional set of π-bonding and antibonding orbitals culminating after the addition of the sixth fluorine with a new set of π-aromatic-like orbitals that affect the molecule in a way that we will refer to hereafter as "fluoromaticity". Depending on the number and position of the fluorine atoms, the contributed π-orbitals can even further stabilize the ring leading to smaller bond lengths within the ring and higher resistance to addition reactions. This added ring stability partially explains the high thermostability and chemical resistance found in polymers containing fluorinated aromatics in their architecture. A similar molecular orbital effect is seen with the addition of other halogen atoms to aromatic rings, though to a much smaller degree and not resulting in the additional ring stability.
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