A1 Journal article (refereed)
Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+ halogen bond by host–guest complexation (2016)


Puttreddy, R., Beyeh, N. K., & Rissanen, K. (2016). Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+ halogen bond by host–guest complexation. CrystEngComm, 18(5), 793-799. https://doi.org/10.1039/C5CE02354H


JYU authors or editors


Publication details

All authors or editors: Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Rissanen, Kari

Journal or series: CrystEngComm

ISSN: 1466-8033

eISSN: 1466-8033

Publication year: 2016

Volume: 18

Issue number: 5

Pages range: 793-799

Publisher: Royal Society of Chemistry

Place of Publication: Cambridge

Publication country: United Kingdom

Publication language: English

DOI: https://doi.org/10.1039/C5CE02354H

Publication open access: Other way freely accessible online

Publication channel open access:

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/50665


Abstract

C ethyl-2-Methylresorcinarene forms host–guest complexes with aromatic N-oxides through multiple intra- and intermolecular hydrogen bonds and C–H⋯π interactions. The host shows conformational flexibility to accommodate 3-methylpyridine N-oxide, while retaining a crown conformation for 2-methyl- and 4-methoxypyridine N-oxides highlighting the substituent effect of the guest. N-Methylmorpholine N-oxide, a 6-membered ring aliphatic N-oxide with a methyl at the N-oxide nitrogen, is bound by the equatorial −N–CH3 group located deep in the cavity. 2-Iodopyridine N-oxide is the only guest that manifests intermolecular N–O⋯I–C halogen bond interactions, which are broken down by the host resulting in a 2 : 2 pseudocapsular complex stabilized by additional C–I⋯π interactions between the two 2-iodopyridine N-oxides located in two adjacent hosts. These host–guest complexes were analyzed in the solid state by single crystal X-ray crystallography and in solution by 1H NMR spectroscopy.


Keywords: supramolecular chemistry; chemical bonds

Free keywords: host–guest complexation; halogen bond; Cethyl-2-methylresorcinarene; pyridine N-oxides


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Ministry reporting: Yes

Reporting Year: 2016

JUFO rating: 1


Last updated on 2021-18-06 at 18:51