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

Authors

Rakesh Puttreddy, University of Jyväskylä
Ngong Kodiah Beyeh, Aalto University
Pia Jurček, University of Jyväskylä
Lotta Turunen, University of Jyväskylä
John F. Trant, University of Windsor
Robin H.A. Ras, Aalto University
Kari Rissanen, University of Jyväskylä

Document Type

Article

Publication Date

6-3-2018

Publication Title

Supramolecular Chemistry

Volume

30

Issue

5-6

First Page

445

Keywords

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

Last Page

454

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.

DOI

10.1080/10610278.2017.1414217

ISSN

10610278

E-ISSN

10290478

Recommended Citation

Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Jurček, Pia; Turunen, Lotta; Trant, John F.; Ras, Robin H.A.; and Rissanen, Kari. (2018). Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides^*. Supramolecular Chemistry, 30 (5-6), 445-454.
https://scholar.uwindsor.ca/chemistrybiochemistrypub/196