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Issue 18, 2014
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Deprotonation of resorcinarenes by mono- and diamine bases: complexation and intermolecular interactions in the solid state

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Abstract

The deprotonation of resorcinarenes by mono- and dibasic amines, viz. triethylamine (TEA) and its dibasic analogue, N,N′-dimethylpiperazine (DMPip), was studied and the resulting supramolecular complexes were analysed in the solid state, in solution and in the gas phase. In the solid state, 1 : 1 (2TEAH+·(ethyl-resorcinarene)2−·MeOH), 3 : 2 [DMPip·2DMPipH+·2(ethyl-resorcinarene)] and 3 : 2 [2DMPip·DMPipH22+@(2methyl-ethyl-resorcinarene)2·2MeOH] solid state complexes and interesting resorcinarene⋯resorcinarene supramolecular networks formed via enhanced hydrogen bonds involving the hydroxyl groups and the deprotonated hydroxyl groups of the resorcinarenes were observed. The host–guest complexes manifest multiple cation⋯π and C–H⋯π interactions as in neutral resorcinarene inclusion complexes. The deprotonation of the resorcinarenes was observed in solution through titration studies. In the gas phase, the deprotonation of the resorcinarene and the encapsulation of the resulting ammonium ions were observed in the negative and positive ion modes, respectively.

Graphical abstract: Deprotonation of resorcinarenes by mono- and diamine bases: complexation and intermolecular interactions in the solid state

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Supplementary files

Article information


Submitted
10 Nov 2013
Accepted
11 Dec 2013
First published
13 Dec 2013

CrystEngComm, 2014,16, 3758-3764
Article type
Paper
Author version available

Deprotonation of resorcinarenes by mono- and diamine bases: complexation and intermolecular interactions in the solid state

N. K. Beyeh, A. Valkonen and K. Rissanen, CrystEngComm, 2014, 16, 3758
DOI: 10.1039/C3CE42291G

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