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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...

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Autores principales: Kysliak, Oleksandr, Schreiner, Simon H. F., Grabicki, Niklas, Liebing, Phil, Weigend, Florian, Dumele, Oliver, Kretschmer, Robert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
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.
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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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