Inclusion complexes of Cethyl-2-methylresorcinarene and pyridine N-oxides: breaking the C–I⋯−O–N+ halogen bond by host–guest complexation
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
© the Authors, 2016. The journal is © The Royal Society of Chemistry 2016. This is an open access article distributed under a Creative Commons Attribution 3.0 Unported Licence.
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.
PublisherRoyal Society of Chemistry
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Related funder(s)Academy of Finland
Funding program(s)Research post as Academy Professor, AoF
Additional information about fundingThe Academy of Finland (K. R.: grant no. 265328 and 263256; N. K. B.: grant no. 258653), the University of Jyvaskyla and Aalto University are gratefully acknowledged for financial support.
Except where otherwise noted, this item's license is described as © the Authors, 2016. The journal is © The Royal Society of Chemistry 2016. This is an open access article distributed under a Creative Commons Attribution 3.0 Unported Licence.
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