Host-Guest Complexes of C-Ethyl-2-methylresorcinarene and Aromatic N,N′-Dioxides

Rakesh Puttreddy, Ngong Kodiah Beyeh, Robin H A Ras, Kari Rissanen*

*Corresponding author for this work

Research output: Contribution to journalArticleScientificpeer-review

4 Citations (Scopus)
90 Downloads (Pure)

Abstract

The C-ethyl-2-methylresorcinarene (1) forms 1:1 in-cavity complexes with aromatic N,N′-dioxides, only if each of the aromatic rings has an N-O group. The structurally different C-shaped 2,2′-bipyridine N,N′-dioxide (2,2′-BiPyNO) and the linear rod-shaped 4,4′-bipyridine N,N′-dioxide (4,4′-BiPyNO) both form 1:1 in-cavity complexes with the host resorcinarene in C4v crown and C2v conformations, respectively. In the solid state, the host-guest interactions between the 1,3-bis(4-pyridyl)propane N,N′-dioxide (BiPyPNO) and the host 1 stabilize the unfavorable anti-gauche conformation. Contrary to the N,N′-dioxide guests, the mono-N-oxide guest, 4-phenylpyridine N-oxide (4PhPyNO), does not form an in-cavity complex in the solid state. The host-guest complexation and the relative guest affinities were studied through 1HNMR competition experiments in methanol. Single-crystal X-ray crystallography of the 1:1 complexes supports the proposed solution-state structures, also revealing strong hydrogen bonds between the host and the guests, not observed in solution owing to hydrogen/deuterium (H/D) exchange processes in methanol.

Original languageEnglish
Pages (from-to)417–423
JournalChemistryOpen
Volume6
Issue number3
DOIs
Publication statusPublished - 2017
MoE publication typeA1 Journal article-refereed

Keywords

  • Conformation
  • N,N′-dioxides
  • Resorcinarenes
  • Supramolecular chemistry
  • Weak interactions

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