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

ABSTRACT: 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).

SUBMITTER: Eckelmann J

PROVIDER: S-EPMC3302070 | biostudies-literature | 2012

REPOSITORIES: biostudies-literature

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

Eckelmann Jens J Saggiomo Vittorio V Fischmann Svenja S Lüning Ulrich U

Beilstein journal of organic chemistry 20120103

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 ...[more]

PMID: 22423268

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