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Issue 3, 2016
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High pressure used for producing a new solvate of 1,4-diazabicyclo[2.2.2]octane hydroiodide

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Abstract

High pressure efficiently induces polymorphic transformations and various solvates of 1,4-diazabicyclo[2.2.2]octane hydroiodide (dabcoHI). However, it has defied the formation of solvates with methanol. In this article we report on the isochoric crystallization method of producing dabcoHI from methanol:ethanol:water solution above 3 GPa leading to the mixed solvate with methanol, albeit with water as well. A single crystal of dabcoHI·H2O·CH3OH has been grown in situ in a diamond-anvil cell, and its structure determined by X-ray diffraction. In its structure the NH+⋯N hydrogen bonds, which link the dabco cations into chains in all 10 unsolvated dabcoHI polymorphs, are replaced by H-bonds NH+⋯OH⋯N analogous to those in two high-pressure polymorphs of monohydrate dabcoHI·H2O. The pressure-induced solvation of dabcoHI has been linked to the dimension of voids in the neat compound, and the systematic pressure effect destabilizing the NH+⋯N bonds has been demonstrated for the series of dabcoHI polymorphs and solvates.

Graphical abstract: High pressure used for producing a new solvate of 1,4-diazabicyclo[2.2.2]octane hydroiodide

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Publication details

The article was received on 26 Jun 2015, accepted on 26 Nov 2015 and first published on 02 Dec 2015


Article type: Paper
DOI: 10.1039/C5NJ01654A
Citation: New J. Chem., 2016,40, 2014-2020
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    High pressure used for producing a new solvate of 1,4-diazabicyclo[2.2.2]octane hydroiodide

    A. Olejniczak, M. Podsiadło and A. Katrusiak, New J. Chem., 2016, 40, 2014
    DOI: 10.1039/C5NJ01654A

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