The Role of Weak Interactions in Supramolecular Compounds: A Synthetic and Theoretical Study of Novel Elongated Cavitands

Tímea Kégl, György Csekő, Gábor Mikle, Anikó Takátsy, L. Kollár, T. Kégl

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A new resorcinol-based tetraazidocavitand (2) has been prepared via substitution reaction started from the corresponding tetrabromocavitand (1). This tetraazidocavitand was used as a starting material for azide-alkyne cycloaddition with different alkynes and this way four novel deepened cavitands have been synthesized under mild conditions. Molecular dynamics, semiempirical PM6 and DFT PBEPBE/6-31G(d,p) studies have been carried out for these new triazole ring containing structures to reveal the exact geometry in solution, furthermore theoretical NMR chemical shift calculations were completed at B3LYP−D3/6-31G(d,p) GIAO level in order to compare with the experimental NMR data. QTAIM analysis at B3LYP−D3/def2-TZVP level was performed and NCI isosurfaces were generated to reveal the potential intramolecular weak interactions between the cavitand branches.

Original languageEnglish
Pages (from-to)8337-8345
Number of pages9
Issue number27
Publication statusPublished - Jan 1 2017



  • Azide-alkyne cycloaddition
  • cavitand
  • DFT calculation
  • NCI isosurfaces
  • QTAIM analysis

ASJC Scopus subject areas

  • Chemistry(all)

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