Halogen-Bonded Co-Crystals of Aromatic N-oxides : Polydentate Acceptors for Halogen and Hydrogen Bonds
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
© 2017 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
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. ...
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Related funder(s)Academy of Finland
Funding program(s)Research post as Academy Professor, AoF; Research costs of Academy Professor, AoF; Postdoctoral Researcher, AoF
Additional information about fundingThe authors gratefully acknowledge financial support from the Academy of Finland (R.P. grant no. 298817, K.R.: grant nos. 265328, 263256, and 292746; N.K.B.: grant no. 258653, R.H.A.R.: grant no. 272579), the University of Jyvaskyla, and Aalto University. This work was supported by the Academy of Finland through its Centres of Excellence Programme (HYBER 2014-2019).
Except where otherwise noted, this item's license is described as © 2017 by the authors. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license.
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