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Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation
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SYSNO ASEP 0535708 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Chiral anion recognition using calix[4]arene-based ureido receptors in a 1,3-alternate conformation Author(s) Horáčková, T. (CZ)
Budka, J. (CZ)
Eigner, V. (CZ)
Chung, W.-S. (TH)
Cuřínová, Petra (UCHP-M) RID, SAI, ORCID
Lhoták, P. (CZ)Source Title Beilstein Journal of Organic Chemistry. - : Beilstein - Institut zur Foerderung der Chemischen Wissenschaften - ISSN 1860-5397
Roč. 16, DEC 7 (2020), s. 2999-3007Number of pages 9 s. Language eng - English Country DE - Germany Keywords anion recognition ; calixarene ; chiral receptor Subject RIV CC - Organic Chemistry OECD category Organic chemistry R&D Projects GA20-07833S GA ČR - Czech Science Foundation (CSF) Method of publishing Open access Institutional support UCHP-M - RVO:67985858 UT WOS 000598575900001 EID SCOPUS 85099218964 DOI 10.3762/bjoc.16.249 Annotation The introduction of chiral alkyl substituents into the lower rim of calix[4]arene immobilised in the 1,3-alternate conformation led to a system possessing a preorganised ureido cavity hemmed with chiral alkyl units in the near proximity. As shown by the 1H NMR titration experiments, these compounds can be used as receptors for chiral anions in DMSO-d6. The chiral recognition ability can be further strengthened by the introduction of another chiral moiety directly onto the urea N atoms. The systems with double chiral units being located around the binding ureido cavity showed better stereodiscrimination, with the highest selectivity factor being 3.33 (KL/KD) achieved for N-acetyl-ʟ-phenylalaninate. The structures of some receptors were confirmed by single crystal X-ray analysis. Workplace Institute of Chemical Process Fundamentals Contact Eva Jirsová, jirsova@icpf.cas.cz, Tel.: 220 390 227 Year of Publishing 2021 Electronic address https://www.beilstein-journals.org/s/zhaeT9EkPh
Number of the records: 1