A1 Journal article (refereed)
Host-Guest Complexes of C-Ethyl-2-methylresorcinarene and Aromatic N,N′-Dioxides (2017)
Puttreddy, R., Beyeh, N. K., Ras, R. H. A., & Rissanen, K. (2017). Host-Guest Complexes of C-Ethyl-2-methylresorcinarene and Aromatic N,N′-Dioxides. ChemistryOpen, 6(3), 417-423. https://doi.org/10.1002/open.201700026
JYU authors or editors
Publication details
All authors or editors: Puttreddy, Rakesh; Beyeh, Ngong Kodiah; Ras, Robin H. A.; Rissanen, Kari
Journal or series: ChemistryOpen
ISSN: 2191-1363
eISSN: 2191-1363
Publication year: 2017
Volume: 6
Issue number: 3
Pages range: 417-423
Publisher: Wiley-VCH-Verlag
Publication country: Germany
Publication language: English
DOI: https://doi.org/10.1002/open.201700026
Publication open access: Openly available
Publication channel open access: Open Access channel
Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/54766
Abstract
The C‐ethyl‐2‐methylresorcinarene (1) forms 1:1 in‐cavity complexes with aromatic N,N′‐dioxides, only if each of the aromatic rings has an N−O group. The structurally different C‐shaped 2,2′‐bipyridine N,N′‐dioxide (2,2′‐BiPyNO) and the linear rod‐shaped 4,4′‐bipyridine N,N′‐dioxide (4,4′‐BiPyNO) both form 1:1 in‐cavity complexes with the host resorcinarene in C4v crown and C2v conformations, respectively. In the solid state, the host–guest interactions between the 1,3‐bis(4‐pyridyl)propane N,N′‐dioxide (BiPyPNO) and the host 1 stabilize the unfavorable anti‐gauche conformation. Contrary to the N,N′‐dioxide guests, the mono‐N‐oxide guest, 4‐phenylpyridine N‐oxide (4PhPyNO), does not form an in‐cavity complex in the solid state. The host–guest complexation and the relative guest affinities were studied through 1H NMR competition experiments in methanol. Single‐crystal X‐ray crystallography of the 1:1 complexes supports the proposed solution‐state structures, also revealing strong hydrogen bonds between the host and the guests, not observed in solution owing to hydrogen/deuterium (H/D) exchange processes in methanol.
Keywords: supramolecular chemistry
Free keywords: conformation; N,N′-dioxides; resorcinarenes; weak interactions
Contributing organizations
Related projects
- Halogen bond: A strong and reliable alternative to coordination bond.
- Puttreddy, Rakesh
- Research Council of Finland
- Weak Interactions as Structural Elements in Self-assembling Molecular Systems
- Rissanen, Kari
- Research Council of Finland
- Weak Interactions as Structural Elements in Self-assembling Molecular Systems (research costs)
- Rissanen, Kari
- Research Council of Finland
Ministry reporting: Yes
Reporting Year: 2017
JUFO rating: 1