Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit

A bi-macrocycle with an incorporated isophthalamide substructure was synthesized by double amide formation between an isophthaloyl dichloride and two equivalents of a bis(alkenyloxy)aniline, followed by ring-closing metathesis and hydrogenation. In contrast to many related isophthalamides, the conca...

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Autores principales: Eckelmann, Jens, Saggiomo, Vittorio, Fischmann, Svenja, Lüning, Ulrich
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302070/
https://www.ncbi.nlm.nih.gov/pubmed/22423268
http://dx.doi.org/10.3762/bjoc.8.2
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author Eckelmann, Jens
Saggiomo, Vittorio
Fischmann, Svenja
Lüning, Ulrich
author_facet Eckelmann, Jens
Saggiomo, Vittorio
Fischmann, Svenja
Lüning, Ulrich
author_sort Eckelmann, Jens
collection PubMed
description A bi-macrocycle with an incorporated isophthalamide substructure was synthesized by double amide formation between an isophthaloyl dichloride and two equivalents of a bis(alkenyloxy)aniline, followed by ring-closing metathesis and hydrogenation. In contrast to many related isophthalamides, the concave host exhibits a better binding for oxides, such as DMSO or pyridine-N-oxide, than for halide anions. A general method for a quick estimation of the strength of binding derived from only a few data points is presented and gives an estimated K(ass) of pyridine-N-oxide of ca. 40 M(−1), NMR titration confirms 25 M(−1).
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spelling pubmed-33020702012-03-15 Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit Eckelmann, Jens Saggiomo, Vittorio Fischmann, Svenja Lüning, Ulrich Beilstein J Org Chem Full Research Paper A bi-macrocycle with an incorporated isophthalamide substructure was synthesized by double amide formation between an isophthaloyl dichloride and two equivalents of a bis(alkenyloxy)aniline, followed by ring-closing metathesis and hydrogenation. In contrast to many related isophthalamides, the concave host exhibits a better binding for oxides, such as DMSO or pyridine-N-oxide, than for halide anions. A general method for a quick estimation of the strength of binding derived from only a few data points is presented and gives an estimated K(ass) of pyridine-N-oxide of ca. 40 M(−1), NMR titration confirms 25 M(−1). Beilstein-Institut 2012-01-03 /pmc/articles/PMC3302070/ /pubmed/22423268 http://dx.doi.org/10.3762/bjoc.8.2 Text en Copyright © 2012, Eckelmann et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Eckelmann, Jens
Saggiomo, Vittorio
Fischmann, Svenja
Lüning, Ulrich
Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
title Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
title_full Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
title_fullStr Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
title_full_unstemmed Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
title_short Binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
title_sort binding of group 15 and group 16 oxides by a concave host containing an isophthalamide unit
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3302070/
https://www.ncbi.nlm.nih.gov/pubmed/22423268
http://dx.doi.org/10.3762/bjoc.8.2
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