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Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane
The aryltellurenyl cation [2‐(tBuNCH)C(6)H(4)Te](+), a Lewis super acid, and the weakly coordinating carborane anion [CB(11)H(12)](−), an extremely weak Brønsted acid (pK (a)=131.0 in MeCN), form an isolable ion pair complex [2‐(tBuNCH)C(6)H(4)Te][CB(11)H(12)], in which the Brønsted acidity (pK (a)...
Autores principales: | , , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8596995/ https://www.ncbi.nlm.nih.gov/pubmed/34495561 http://dx.doi.org/10.1002/chem.202103181 |
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author | Hejda, Martin Duvinage, Daniel Lork, Enno Lyčka, Antonín Černošek, Zdeněk Macháček, Jan Makarov, Sergey Ketkov, Sergey Mebs, Stefan Dostál, Libor Beckmann, Jens |
author_facet | Hejda, Martin Duvinage, Daniel Lork, Enno Lyčka, Antonín Černošek, Zdeněk Macháček, Jan Makarov, Sergey Ketkov, Sergey Mebs, Stefan Dostál, Libor Beckmann, Jens |
author_sort | Hejda, Martin |
collection | PubMed |
description | The aryltellurenyl cation [2‐(tBuNCH)C(6)H(4)Te](+), a Lewis super acid, and the weakly coordinating carborane anion [CB(11)H(12)](−), an extremely weak Brønsted acid (pK (a)=131.0 in MeCN), form an isolable ion pair complex [2‐(tBuNCH)C(6)H(4)Te][CB(11)H(12)], in which the Brønsted acidity (pK (a) 7.4 in MeCN) of the formally hydridic B−H bonds is dramatically increased by more than 120 orders of magnitude. The electrophilic activation of B−H bonds in the carborane moiety gives rise to a proton transfer from boron to nitrogen at slightly elevated temperatures, as rationalized by the isolation of a mixture of the zwitterionic isomers 12‐ and 7‐[2‐(tBuN{H}CH)C(6)H(4)Te(CB(11)H(11))] in ratios ranging from 62 : 38 to 80 : 20. |
format | Online Article Text |
id | pubmed-8596995 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
spelling | pubmed-85969952021-11-22 Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane Hejda, Martin Duvinage, Daniel Lork, Enno Lyčka, Antonín Černošek, Zdeněk Macháček, Jan Makarov, Sergey Ketkov, Sergey Mebs, Stefan Dostál, Libor Beckmann, Jens Chemistry Communications The aryltellurenyl cation [2‐(tBuNCH)C(6)H(4)Te](+), a Lewis super acid, and the weakly coordinating carborane anion [CB(11)H(12)](−), an extremely weak Brønsted acid (pK (a)=131.0 in MeCN), form an isolable ion pair complex [2‐(tBuNCH)C(6)H(4)Te][CB(11)H(12)], in which the Brønsted acidity (pK (a) 7.4 in MeCN) of the formally hydridic B−H bonds is dramatically increased by more than 120 orders of magnitude. The electrophilic activation of B−H bonds in the carborane moiety gives rise to a proton transfer from boron to nitrogen at slightly elevated temperatures, as rationalized by the isolation of a mixture of the zwitterionic isomers 12‐ and 7‐[2‐(tBuN{H}CH)C(6)H(4)Te(CB(11)H(11))] in ratios ranging from 62 : 38 to 80 : 20. John Wiley and Sons Inc. 2021-09-28 2021-10-21 /pmc/articles/PMC8596995/ /pubmed/34495561 http://dx.doi.org/10.1002/chem.202103181 Text en © 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Communications Hejda, Martin Duvinage, Daniel Lork, Enno Lyčka, Antonín Černošek, Zdeněk Macháček, Jan Makarov, Sergey Ketkov, Sergey Mebs, Stefan Dostál, Libor Beckmann, Jens Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane |
title | Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane |
title_full | Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane |
title_fullStr | Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane |
title_full_unstemmed | Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane |
title_short | Lewis Superacidic Tellurenyl Cation‐Induced Electrophilic Activation of an Inert Carborane |
title_sort | lewis superacidic tellurenyl cation‐induced electrophilic activation of an inert carborane |
topic | Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8596995/ https://www.ncbi.nlm.nih.gov/pubmed/34495561 http://dx.doi.org/10.1002/chem.202103181 |
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