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A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons
Many chemicals known today are partially or fully aromatic, since a ring framework experiences additional stabilization through the delocalization of π‐electrons. While aromatic rings with equal numbers of π‐electrons and ring atoms such as benzene are particularly stable, those with the minimally r...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2022
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401857/ https://www.ncbi.nlm.nih.gov/pubmed/35593009 http://dx.doi.org/10.1002/anie.202206963 |
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author | Kysliak, Oleksandr Schreiner, Simon H. F. Grabicki, Niklas Liebing, Phil Weigend, Florian Dumele, Oliver Kretschmer, Robert |
author_facet | Kysliak, Oleksandr Schreiner, Simon H. F. Grabicki, Niklas Liebing, Phil Weigend, Florian Dumele, Oliver Kretschmer, Robert |
author_sort | Kysliak, Oleksandr |
collection | PubMed |
description | Many chemicals known today are partially or fully aromatic, since a ring framework experiences additional stabilization through the delocalization of π‐electrons. While aromatic rings with equal numbers of π‐electrons and ring atoms such as benzene are particularly stable, those with the minimally required two π‐electrons are very rare and yet remain limited to three‐ and four‐membered rings if not stabilized in the coordination sphere of heavy metals. Here we report the facile synthesis of a dipotassium cyclopentagallene, a unique example of a five‐membered aromatic ring stabilized by only two π‐electrons. Single‐crystal X‐ray diffraction revealed a planar Ga(5) ring with almost equal gallium–gallium bond lengths, which together with computational and spectroscopic data confirm its aromatic character. Our results prove that aromatic stabilization goes far beyond what has previously been assumed as minimum π‐electron count in a five‐atom ring fragment. |
format | Online Article Text |
id | pubmed-9401857 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-94018572022-08-26 A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons Kysliak, Oleksandr Schreiner, Simon H. F. Grabicki, Niklas Liebing, Phil Weigend, Florian Dumele, Oliver Kretschmer, Robert Angew Chem Int Ed Engl Communications Many chemicals known today are partially or fully aromatic, since a ring framework experiences additional stabilization through the delocalization of π‐electrons. While aromatic rings with equal numbers of π‐electrons and ring atoms such as benzene are particularly stable, those with the minimally required two π‐electrons are very rare and yet remain limited to three‐ and four‐membered rings if not stabilized in the coordination sphere of heavy metals. Here we report the facile synthesis of a dipotassium cyclopentagallene, a unique example of a five‐membered aromatic ring stabilized by only two π‐electrons. Single‐crystal X‐ray diffraction revealed a planar Ga(5) ring with almost equal gallium–gallium bond lengths, which together with computational and spectroscopic data confirm its aromatic character. Our results prove that aromatic stabilization goes far beyond what has previously been assumed as minimum π‐electron count in a five‐atom ring fragment. John Wiley and Sons Inc. 2022-06-23 2022-08-01 /pmc/articles/PMC9401857/ /pubmed/35593009 http://dx.doi.org/10.1002/anie.202206963 Text en © 2022 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH https://creativecommons.org/licenses/by-nc/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ (https://creativecommons.org/licenses/by-nc/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes. |
spellingShingle | Communications Kysliak, Oleksandr Schreiner, Simon H. F. Grabicki, Niklas Liebing, Phil Weigend, Florian Dumele, Oliver Kretschmer, Robert A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons |
title | A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons |
title_full | A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons |
title_fullStr | A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons |
title_full_unstemmed | A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons |
title_short | A Planar Five‐Membered Aromatic Ring Stabilized by Only Two π‐Electrons |
title_sort | planar five‐membered aromatic ring stabilized by only two π‐electrons |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9401857/ https://www.ncbi.nlm.nih.gov/pubmed/35593009 http://dx.doi.org/10.1002/anie.202206963 |
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