A1 Journal article (refereed)
Host-guest complexes of C-propyl-2-bromoresorcinarene with aromatic N-oxides (2018)

Puttreddy, R., Beyeh, N. K., Jurček, P., Turunen, L., Trant, J. F., Ras, R. H. A., & Rissanen, K. (2018). 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

JYU authors or editors

Puttreddy, Rakesh
Turunen, Lotta
Rissanen, Kari

Publication details

All authors or editors: Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Jurček, Pia; Turunen, Lotta; Trant, John F.; Ras, Robin H. A.; Rissanen, Kari

Journal or series: Supramolecular Chemistry

ISSN: 1061-0278

eISSN: 1026-7816

Publication year: 2018

Volume: 30

Issue number: 5-6

Pages range: 445-454

Publisher: Taylor & Francis

Place of Publication: Abingdon

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1080/10610278.2017.1414217

Publication open access: Not open

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/58323

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.

Keywords: crystals; chemistry; molecules; hydrogen; supramolecular chemistry; hydrogen bonds

Free keywords: resorcinarenes; aromatic N-oxides; crystal structure

Fields of science: