3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives

A large number of 2D/2D and 3D/3D aromatic fusions that keep their aromaticity in the fused compounds have been synthesized. In addition, we have previously proven the electronic relationship between the 3D aromaticity of boron hydrides and the 2D aromaticity of PAHs. Here we report the possible exi...

Descripción completa

Detalles Bibliográficos
Autores principales: Poater, Jordi, Viñas, Clara, Solà, Miquel, Teixidor, Francesc
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group UK 2022
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9253344/
https://www.ncbi.nlm.nih.gov/pubmed/35788134
http://dx.doi.org/10.1038/s41467-022-31267-7
_version_ 1784740463216951296
author Poater, Jordi
Viñas, Clara
Solà, Miquel
Teixidor, Francesc
author_facet Poater, Jordi
Viñas, Clara
Solà, Miquel
Teixidor, Francesc
author_sort Poater, Jordi
collection PubMed
description A large number of 2D/2D and 3D/3D aromatic fusions that keep their aromaticity in the fused compounds have been synthesized. In addition, we have previously proven the electronic relationship between the 3D aromaticity of boron hydrides and the 2D aromaticity of PAHs. Here we report the possible existence of 3D/2D aromatic fusions that retain the whole aromaticity of the two units. Our conclusion is that such a 3D/2D aromatic combination is not possible due to the ineffective overlap between the π-MOs of the planar species and the n + 1 molecular orbitals in the aromatic cage that deter an effective electronic delocalization between the two fused units. We have also proven the necessary conditions for 3D/3D fusions to take place, and how aromaticity of each unit is decreased in 2D/2D and 3D/3D fusions.
format Online
Article
Text
id pubmed-9253344
institution National Center for Biotechnology Information
language English
publishDate 2022
publisher Nature Publishing Group UK
record_format MEDLINE/PubMed
spelling pubmed-92533442022-07-06 3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives Poater, Jordi Viñas, Clara Solà, Miquel Teixidor, Francesc Nat Commun Article A large number of 2D/2D and 3D/3D aromatic fusions that keep their aromaticity in the fused compounds have been synthesized. In addition, we have previously proven the electronic relationship between the 3D aromaticity of boron hydrides and the 2D aromaticity of PAHs. Here we report the possible existence of 3D/2D aromatic fusions that retain the whole aromaticity of the two units. Our conclusion is that such a 3D/2D aromatic combination is not possible due to the ineffective overlap between the π-MOs of the planar species and the n + 1 molecular orbitals in the aromatic cage that deter an effective electronic delocalization between the two fused units. We have also proven the necessary conditions for 3D/3D fusions to take place, and how aromaticity of each unit is decreased in 2D/2D and 3D/3D fusions. Nature Publishing Group UK 2022-07-04 /pmc/articles/PMC9253344/ /pubmed/35788134 http://dx.doi.org/10.1038/s41467-022-31267-7 Text en © The Author(s) 2022 https://creativecommons.org/licenses/by/4.0/Open Access This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Article
Poater, Jordi
Viñas, Clara
Solà, Miquel
Teixidor, Francesc
3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives
title 3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives
title_full 3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives
title_fullStr 3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives
title_full_unstemmed 3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives
title_short 3D and 2D aromatic units behave like oil and water in the case of benzocarborane derivatives
title_sort 3d and 2d aromatic units behave like oil and water in the case of benzocarborane derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9253344/
https://www.ncbi.nlm.nih.gov/pubmed/35788134
http://dx.doi.org/10.1038/s41467-022-31267-7
work_keys_str_mv AT poaterjordi 3dand2daromaticunitsbehavelikeoilandwaterinthecaseofbenzocarboranederivatives
AT vinasclara 3dand2daromaticunitsbehavelikeoilandwaterinthecaseofbenzocarboranederivatives
AT solamiquel 3dand2daromaticunitsbehavelikeoilandwaterinthecaseofbenzocarboranederivatives
AT teixidorfrancesc 3dand2daromaticunitsbehavelikeoilandwaterinthecaseofbenzocarboranederivatives

Ejemplares similares