Selective Carboxylate Recognition Using Urea-Functionalized Unclosed Cryptands: Mild Synthesis and Complexation Studies

The Journal of Organic Chemistry
Patryk NiedbałaJanusz Jurczak

Abstract

Herein we present the synthesis and evaluation of anion-binding properties of 12 new receptors from the unclosed cryptand family. Their core is built on the stable 26-membered tetraamidic macrocyclic scaffold, whereas various alkyl and aryl urea substituents were introduced after a yield-limiting macrocyclization step (65-98%). The receptors strongly bind anions, in particular carboxylates, even in a highly competitive solvent mixture (DMSO-d6 + H2O 95:5 v/v).

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Citations

Apr 4, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Patryk NiedbałaJanusz Jurczak
Jun 3, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Kajetan DąbrowaJanusz Jurczak

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Methods Mentioned

BETA
NMR
column chromatography

Software Mentioned

Spartan ’
HypNMR

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