Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*

Rakesh Puttreddy, Ngong Kodiah Beyeh, Pia Jurček, Lotta Turunen, John F. Trant, Robin H.A. Ras, Kari Rissanen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

Abstract

The host-guest complexes of C-propyl-2-bromoresorcinarene with pyridine N-oxide, 3-methylpyridine N-oxide, quinoline N-oxide and isoquinoline N-oxide are studied using single crystal X-ray crystallography and 1H NMR spectroscopy. The C-propyl-2-bromoresorcinarene forms endo-complexes with the aromatic N-oxides in the solid-state when crystallised from either methanol or acetone. In solution, the endo-complexes were observed only in methanol-d4. In DMSO the solvent itself is a good guest, and crystallisation provides only solvate endo-complexes. The C-propyl-2-bromoresorcinarene shows remarkable flexibility when crystallised from either methanol or acetone, and packs into one-dimensional self-included chains. Of special note, crystallising C-propyl-2-bromoresorcinarene with 3-methylpyridine N-oxide from acetone results in a 2:2 dimeric capsular assembly organised through both C−H···πhost and N−O···(H−O)host interactions.

Original languageEnglish
Pages (from-to)445-454
Number of pages10
JournalSupramolecular Chemistry
Volume30
Issue number5-6
DOIs
Publication statusPublished - 2017
MoE publication typeA1 Journal article-refereed

Keywords

  • aromatic N-oxides
  • crystal structure
  • hydrogen bonds
  • resorcinarenes
  • Supramolecular chemistry

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    Puttreddy, R., Beyeh, N. K., Jurček, P., Turunen, L., Trant, J. F., Ras, R. H. A., & Rissanen, K. (2017). Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides*. Supramolecular Chemistry, 30(5-6), 445-454. https://doi.org/10.1080/10610278.2017.1414217