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

Patryk Niedbała | Zendy; Maciej Majdecki | Zendy; Kajetan Dąbrowa | Zendy; Janusz Jurczak | Zendy

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

Author(s) -

Patryk Niedbała,

Maciej Majdecki,

Kajetan Dąbrowa,

Janusz Jurczak

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b03082

Subject(s) - cryptand , chemistry , urea , alkyl , carboxylate , yield (engineering) , aryl , combinatorial chemistry , competitive binding , receptor , stereochemistry , ion , organic chemistry , materials science , biochemistry , metallurgy

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- d 6 + H 2 O 95:5 v/v).

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