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Fluoromaticity: The Molecular Orbital Contributions of Fluorine Substituents to the π-Systems of Aromatic Rings
[Image: see text] 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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8655763/ https://www.ncbi.nlm.nih.gov/pubmed/34901609 http://dx.doi.org/10.1021/acsomega.1c04175 |
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author | Fuhrer, Timothy J. Houck, Matthew Iacono, Scott T. |
author_facet | Fuhrer, Timothy J. Houck, Matthew Iacono, Scott T. |
author_sort | Fuhrer, Timothy J. |
collection | PubMed |
description | [Image: see text] 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. |
format | Online Article Text |
id | pubmed-8655763 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-86557632021-12-10 Fluoromaticity: The Molecular Orbital Contributions of Fluorine Substituents to the π-Systems of Aromatic Rings Fuhrer, Timothy J. Houck, Matthew Iacono, Scott T. ACS Omega [Image: see text] 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. American Chemical Society 2021-11-23 /pmc/articles/PMC8655763/ /pubmed/34901609 http://dx.doi.org/10.1021/acsomega.1c04175 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/). |
spellingShingle | Fuhrer, Timothy J. Houck, Matthew Iacono, Scott T. Fluoromaticity: The Molecular Orbital Contributions of Fluorine Substituents to the π-Systems of Aromatic Rings |
title | Fluoromaticity: The Molecular Orbital Contributions
of Fluorine Substituents to the π-Systems of Aromatic
Rings |
title_full | Fluoromaticity: The Molecular Orbital Contributions
of Fluorine Substituents to the π-Systems of Aromatic
Rings |
title_fullStr | Fluoromaticity: The Molecular Orbital Contributions
of Fluorine Substituents to the π-Systems of Aromatic
Rings |
title_full_unstemmed | Fluoromaticity: The Molecular Orbital Contributions
of Fluorine Substituents to the π-Systems of Aromatic
Rings |
title_short | Fluoromaticity: The Molecular Orbital Contributions
of Fluorine Substituents to the π-Systems of Aromatic
Rings |
title_sort | fluoromaticity: the molecular orbital contributions
of fluorine substituents to the π-systems of aromatic
rings |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8655763/ https://www.ncbi.nlm.nih.gov/pubmed/34901609 http://dx.doi.org/10.1021/acsomega.1c04175 |
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