Synthesis and conformational behaviour of lower-rim tetraacetylated thiacalix[4]arenes |
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Authors: | Markéta Šimánová Ivan Stibor Pavel Lhoták |
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Institution: | a Department of Organic Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic b Laboratory of NMR Spectroscopy, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic c Department of Solid State Chemistry, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic |
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Abstract: | The acylation of thiacalix4]arenes with AcCl or Ac2O gave the corresponding lower-rim tetraacetoxy derivatives. In contrast to classical calix4]arenes, tetraacetylated thiacalix4]arenes are conformationally mobile in solution and represent a thermodynamic equilibrium of three different conformers at room temperature. As proven by a dynamic 1H NMR study, conformational preferences of acetylated thiacalix4]arenes considerably depend on the upper-rim substitution. Hence, t-Bu thiacalixarene prefers 1,3-alternate and 1,2-alternate conformations (43% and 38%, respectively), while the upper-rim unsubstituted compound adopts preferably the partial cone conformation (70%). |
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