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

Download
COinS