Jump to main content
Jump to site search

Issue 2, 2015
Previous Article Next Article

Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation

Author affiliations

Abstract

While all the alkylation methods commonly used in the chemistry of classical calixarenes failed, tetranitrothiacalix[4]arene was easily alkylated using various alcohols under Mitsunobu reaction conditions. The products thus obtained were immobilized in the 1,3-alternate conformation as suggested by 1H NMR and proven unequivocally by X-ray analysis. The introduction of chiral alkyl substituents into the lower rim of thiacalixarene gave us an opportunity to form well-preorganized ureido cavities on both sites of the system. As revealed by 1H NMR titration experiments, such compounds were capable of chiral anion recognition even in DMSO-d6 which is a highly competitive solvent towards hydrogen bonding interactions. The highest chiral discrimination was achieved for free serine with a selectivity factor of 3.13 for the D-isomer.

Graphical abstract: Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation

Back to tab navigation

Supplementary files

Publication details

The article was received on 04 Nov 2014, accepted on 02 Dec 2014 and first published on 04 Dec 2014


Article type: Paper
DOI: 10.1039/C4NJ01956C
Citation: New J. Chem., 2015,39, 1382-1389
  •   Request permissions

    Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation

    M. Mačková, J. Mikšátko, J. Budka, V. Eigner, P. Cuřínová and P. Lhoták, New J. Chem., 2015, 39, 1382
    DOI: 10.1039/C4NJ01956C

Search articles by author

Spotlight

Advertisements