Anion Binding by Meta Ureido-substituted Thiacalix[4]arenes

0420988 - ÚCHP 2014 RIV GB eng J - Journal Article
Kundrát, O. - Eigner, V. - Cuřínová, Petra - Kroupa, J. - Lhoták, P.
Anion Binding by Meta Ureido-substituted Thiacalix[4]arenes.
Tetrahedron. Roč. 67, č. 43 (2011), s. 8367-8372. ISSN 0040-4020. E-ISSN 1464-5416
R&D Projects: GA ČR GA203/09/0691; GA AV ČR IAAX08240901
Institutional support: RVO:67985858
Keywords : calixarene * meta nitration * recognition
Subject RIV: CC - Organic Chemistry
Impact factor: 3.025, year: 2011

The regioselective nitration of 25,26,27,28-tetrapropoxythiacalix[4]arene (1,3-alternate) led to the formation of mono- and dinitro derivatives bearing NO2 groups in the meta positions at the same side of the molecule. Their reduction and subsequent condensation with arylisocyanates gave the new types of anion receptors with a so far unknown meta-substitution pattern. In a highly HB-competitive solvent like DMSO, the novel ligands showed good complexation abilities. Moreover, as can be documented by higher complexation constants, achiral receptors 9a, 9b are better preorganized for anion binding than corresponding stereoisomers 10a, 10b. Our results indicate that anion receptors based on meta-substituted thiacalixarenes possess complexation abilities fully comparable with common para-substituted analogues.
Permanent Link: http://hdl.handle.net/11104/0227436