A1 Journal article (refereed)
Halogen-Bonded Co-Crystals of Aromatic N-oxides : Polydentate Acceptors for Halogen and Hydrogen Bonds (2017)

Puttreddy, R., Topic, F., Valkonen, A., & Rissanen, K. (2017). Halogen-Bonded Co-Crystals of Aromatic N-oxides : Polydentate Acceptors for Halogen and Hydrogen Bonds. Crystals, 7(7), Article 214. https://doi.org/10.3390/cryst7070214

JYU authors or editors

Publication details

All authors or editors: Puttreddy, Rakesh; Topic, Filip; Valkonen, Arto; Rissanen, Kari

Journal or series: Crystals

ISSN: 2073-4352

eISSN: 2073-4352

Publication year: 2017

Volume: 7

Issue number: 7

Article number: 214

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst7070214

Persistent website address: http://www.mdpi.com/2073-4352/7/7/214

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/54968

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: x-ray crystallography; organic chemistry; hydrogen bonds

Free keywords: halogen bond; hydrogen bond; aromatic N-oxides; perfluoroalkyl; diiodoperfluoroalkanes; polydentate; N−O group; C−; H···O interactions

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Ministry reporting: Yes

Reporting Year: 2017

JUFO rating: 0