Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors

Strong halogen bond (XB) donors are needed for the activation of neutral substrates. We demonstrate that XB donor properties of iodo-triazoles can be significantly enhanced by quaternization in combination with varying the counterion and aromatic substituent, exemplified by association constants wit...

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Autores principales: Peterson, Anna, Kaasik, Mikk, Metsala, Andrus, Järving, Ivar, Adamson, Jasper, Kanger, Tõnis
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063393/
https://www.ncbi.nlm.nih.gov/pubmed/35517004
http://dx.doi.org/10.1039/c9ra01692a
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author Peterson, Anna
Kaasik, Mikk
Metsala, Andrus
Järving, Ivar
Adamson, Jasper
Kanger, Tõnis
author_facet Peterson, Anna
Kaasik, Mikk
Metsala, Andrus
Järving, Ivar
Adamson, Jasper
Kanger, Tõnis
author_sort Peterson, Anna
collection PubMed
description Strong halogen bond (XB) donors are needed for the activation of neutral substrates. We demonstrate that XB donor properties of iodo-triazoles can be significantly enhanced by quaternization in combination with varying the counterion and aromatic substituent, exemplified by association constants with quinuclidine as high as 1.1 × 10(4) M(−1).
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spelling pubmed-90633932022-05-04 Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors Peterson, Anna Kaasik, Mikk Metsala, Andrus Järving, Ivar Adamson, Jasper Kanger, Tõnis RSC Adv Chemistry Strong halogen bond (XB) donors are needed for the activation of neutral substrates. We demonstrate that XB donor properties of iodo-triazoles can be significantly enhanced by quaternization in combination with varying the counterion and aromatic substituent, exemplified by association constants with quinuclidine as high as 1.1 × 10(4) M(−1). The Royal Society of Chemistry 2019-04-15 /pmc/articles/PMC9063393/ /pubmed/35517004 http://dx.doi.org/10.1039/c9ra01692a Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Peterson, Anna
Kaasik, Mikk
Metsala, Andrus
Järving, Ivar
Adamson, Jasper
Kanger, Tõnis
Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
title Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
title_full Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
title_fullStr Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
title_full_unstemmed Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
title_short Tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
title_sort tunable chiral triazole-based halogen bond donors: assessment of donor strength in solution with nitrogen-containing acceptors
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9063393/
https://www.ncbi.nlm.nih.gov/pubmed/35517004
http://dx.doi.org/10.1039/c9ra01692a
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