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Issue 37, 2015
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Application of RDC enhanced NMR spectroscopy in structural analysis of thiacalix[4]arene derivatives

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Abstract

Thiacalix[4]arene spirodienone was rearranged into the corresponding phenoxathiin-based macrocycle. Alkylation of this inherently chiral system to achieve its immobilization led to a mixture of only two (out of four theoretically possible) stereoisomers. As standard NOE and dynamic NMR experiments did not lead to unambiguous determination of the structures we applied the Residual Dipolar Coupling constant (RDC) method. Poly-γ-ethyl-L-glutamate (PELG) and poly-γ-benzyl-L-glutamate (PBLG) were found to be easily applicable lyotropic liquid crystalline alignment media for the conformational analysis of thiacalixarene derivatives. Using these media the 1,2-alternate and the partial cone conformations were determined unequivocally.

Graphical abstract: Application of RDC enhanced NMR spectroscopy in structural analysis of thiacalix[4]arene derivatives

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Publication details

The article was received on 13 Jul 2015, accepted on 30 Jul 2015 and first published on 30 Jul 2015


Article type: Paper
DOI: 10.1039/C5OB01424G
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 9610-9618
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    Application of RDC enhanced NMR spectroscopy in structural analysis of thiacalix[4]arene derivatives

    L. Vrzal, M. Kratochvílová-Šimánová, T. Landovský, K. Polívková, J. Budka, H. Dvořáková and P. Lhoták, Org. Biomol. Chem., 2015, 13, 9610
    DOI: 10.1039/C5OB01424G

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