Journal
TETRAHEDRON
Volume 66, Issue 1, Pages 359-367Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.10.075
Keywords
Molecular recognition; p-tert-Butyl thiacalix[4]arenes; alpha-Hydroxy- and dicarboxylic acids; UV-spectroscopy method
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Funding
- RFBR [09-03-00426, 08-03-90403-Ukr]
- Ministry of Science and Education of Russian Federation
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A series of new p-tert-butyl thiacalix[4]arenes with o-, m-, p-amido and o-, m-, p-(amidomethyl)pyridine substituents at the lower rim in cone, partial cone, and 1,3-alternate conformations were synthesized. The ability of the obtained compounds to recognize the a.-hydroxy (glycolic, tartaric) and dicarboxylic (oxalic, malonic, succinic, fumaric, and maleic) acids was investigated by UV-vis spectroscopy. Also, the efficiency and selectivity of binding, the association constants log K-a (10(2) to 10(7) M-1) and the stoichiometry were determined for the complexes of p-tert-butyl thiacalix[4]arenes with the acids. The receptors based on p-tert-butyl thiacalix[4]arenes with (amidomethyl)pyridine substitutes are most efficient in complexation in many cases. (C) 2009 Elsevier Ltd. All rights reserved.
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