Conformational properties of propargyloxy-calix[4]arene tricarboxamides: NMR and DFT studies on the O -through-the-annulus rotation

János B. Czirok, Ákos Tarcsay, Pál D. Mezei, A. Simon, László Balázs, I. Bitter

Research output: Contribution to journalArticle

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Abstract

The size limit of substituents allowing O-through-the-annulus rotation of substituted calix[4]arenes was further extended to the propargyloxy group in 24-propargyloxy-25,26,27-tris(N,N-dimethylcarbamoylmethoxy)-p-tert-butylcalix[4]arene by demonstrating its free but slow motion affording equilibrium between the partial cone and 1,2-alternate conformers. The effect of solvent and upper rim substituents R1on the conformational inversion was investigated by means of 1H NMR. The rotational isomerisation of the parent (R1= H) analogue could not unambiguously be detected. The experimental results were supported by comprehensive density functional theory studies.

Original languageEnglish
Pages (from-to)722-728
Number of pages7
JournalSupramolecular Chemistry
Volume26
Issue number10-12
DOIs
Publication statusPublished - Dec 1 2014

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Isomerization
Discrete Fourier transforms
Density functional theory
Cones
Nuclear magnetic resonance
calix(4)arene

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Conformational properties of propargyloxy-calix[4]arene tricarboxamides : NMR and DFT studies on the O -through-the-annulus rotation. / Czirok, János B.; Tarcsay, Ákos; Mezei, Pál D.; Simon, A.; Balázs, László; Bitter, I.

In: Supramolecular Chemistry, Vol. 26, No. 10-12, 01.12.2014, p. 722-728.

Research output: Contribution to journalArticle

Czirok, János B. ; Tarcsay, Ákos ; Mezei, Pál D. ; Simon, A. ; Balázs, László ; Bitter, I. / Conformational properties of propargyloxy-calix[4]arene tricarboxamides : NMR and DFT studies on the O -through-the-annulus rotation. In: Supramolecular Chemistry. 2014 ; Vol. 26, No. 10-12. pp. 722-728.
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