Unsubstituted Oxacalix[n]arenes (n=4 and 8): A Conformational Study in Solution and Solid State and Interaction Studies with Aromatic Guests

Anna Peterson, Sandra Kaabel, Iiris Kahn, Tõnis Pehk, Riina Aav*, Jasper Adamson*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

2 Citations (Scopus)

Abstract

We present single crystal structures of unsubstituted oxacalix[4]arene and oxacalix[8]arene macrocycles and investigate the weak supramolecular interactions that govern their packing in the solid state. We further show that the unsubstituted oxacalix[4]arene shows weak complexation with two aromatic guest species, benzoic acid and ferrocene, in CDCl3, whereas the oxacalix[8]arene host does not complex with these guest molecules. We also present NMR titration experiments with non-aromatic acids and DFT calculations that signify the importance of π-π interactions for complexation with benzoic acid. Weak complexation is also observed between electron-rich aromatic guest molecules and the unsubstituted oxacalix[4]arene host.

Original languageEnglish
Pages (from-to)9091-9095
Number of pages5
JournalChemistrySelect
Volume3
Issue number31
DOIs
Publication statusPublished - 23 Aug 2018
MoE publication typeA1 Journal article-refereed

Keywords

  • conformational study
  • host-guest complexation
  • NMR titration
  • nuclear magnetic resonance
  • oxacalix[n]arene
  • single crystal structure

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