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Chiral Anion Recognition by a Ureido-Thiacalix[4]arene Ligand Immobilized in the 1,3-Alternate Conformation
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SYSNO ASEP 0440911 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Chiral Anion Recognition by a Ureido-Thiacalix[4]arene Ligand Immobilized in the 1,3-Alternate Conformation Author(s) Mačková, M. (CZ)
Mikšátko, J. (CZ)
Budka, J. (CZ)
Eigner, V. (CZ)
Cuřínová, Petra (UCHP-M) RID, SAI, ORCID
Lhoták, P. (CZ)Source Title New Journal of Chemistry. - : Royal Society of Chemistry - ISSN 1144-0546
Roč. 39, č. 2 (2015), s. 1382-1389Number of pages 8 s. Language eng - English Country GB - United Kingdom Keywords uncommon regioselectivity ; receptors ; thiacalixarenes Subject RIV CC - Organic Chemistry Institutional support UCHP-M - RVO:67985858 UT WOS 000349222800076 EID SCOPUS 84922455028 DOI 10.1039/c4nj01956c Annotation 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. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2016
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