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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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The article was received on 10 Nov 2013, accepted on 11 Dec 2013 and first published on 13 Dec 2013


Article type: Paper
DOI: 10.1039/C3CE42291G
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Citation: CrystEngComm, 2014,16, 3758-3764
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    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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