Halogen Bonding Helicates Encompassing Iodonium Cations

The first halonium‐ion‐based helices were designed and synthesized using oligo‐aryl/pyridylene‐ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix...

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Autores principales: Vanderkooy, Alan, Gupta, Arvind Kumar, Földes, Tamás, Lindblad, Sofia, Orthaber, Andreas, Pápai, Imre, Erdélyi, Máté
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6773207/
https://www.ncbi.nlm.nih.gov/pubmed/31074942
http://dx.doi.org/10.1002/anie.201904817
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author Vanderkooy, Alan
Gupta, Arvind Kumar
Földes, Tamás
Lindblad, Sofia
Orthaber, Andreas
Pápai, Imre
Erdélyi, Máté
author_facet Vanderkooy, Alan
Gupta, Arvind Kumar
Földes, Tamás
Lindblad, Sofia
Orthaber, Andreas
Pápai, Imre
Erdélyi, Máté
author_sort Vanderkooy, Alan
collection PubMed
description The first halonium‐ion‐based helices were designed and synthesized using oligo‐aryl/pyridylene‐ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X‐ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4‐penten‐1‐ol.
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spelling pubmed-67732072019-10-07 Halogen Bonding Helicates Encompassing Iodonium Cations Vanderkooy, Alan Gupta, Arvind Kumar Földes, Tamás Lindblad, Sofia Orthaber, Andreas Pápai, Imre Erdélyi, Máté Angew Chem Int Ed Engl Communications The first halonium‐ion‐based helices were designed and synthesized using oligo‐aryl/pyridylene‐ethynylene backbones that fold around reactive iodonium ions. Halogen bonding interactions stabilize the iodonium ions within the helices. Remarkably, the distance between two iodonium ions within a helix is shorter than the sum of their van der Waals radii. The helical conformations were characterized by X‐ray crystallography in the solid state, by NMR spectroscopy in solution and corroborated by DFT calculations. The helical complexes possess potential synthetic utility, as demonstrated by their ability to induce iodocyclization of 4‐penten‐1‐ol. John Wiley and Sons Inc. 2019-06-06 2019-07-01 /pmc/articles/PMC6773207/ /pubmed/31074942 http://dx.doi.org/10.1002/anie.201904817 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://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
Vanderkooy, Alan
Gupta, Arvind Kumar
Földes, Tamás
Lindblad, Sofia
Orthaber, Andreas
Pápai, Imre
Erdélyi, Máté
Halogen Bonding Helicates Encompassing Iodonium Cations
title Halogen Bonding Helicates Encompassing Iodonium Cations
title_full Halogen Bonding Helicates Encompassing Iodonium Cations
title_fullStr Halogen Bonding Helicates Encompassing Iodonium Cations
title_full_unstemmed Halogen Bonding Helicates Encompassing Iodonium Cations
title_short Halogen Bonding Helicates Encompassing Iodonium Cations
title_sort halogen bonding helicates encompassing iodonium cations
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6773207/
https://www.ncbi.nlm.nih.gov/pubmed/31074942
http://dx.doi.org/10.1002/anie.201904817
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