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Issue 9, 2010
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Pressure induced transformations of 1,4-diazabicyclo[2.2.2]octane (dabco) hydroiodide: diprotonation of dabco, its N-methylation and co-crystallization with methanol

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Abstract

The non-solvated crystals of 1,4-diazabicyclo[2.2.2]octane hydroiodide (dabcoHI, [C6H13N2]+I) obtained at normal conditions are hexagonal and exhibit giant dielectric response and anisotropic relaxer properties. The isochoric crystallization of dabcoHI at 1.80 GPa yields non-solvated dabcoHI crystal and a [C6H14N2]2+2I:3CH3OH solvate (dabco2HI:3CH3OH) solvate, while pressure exceeding 2.30 GPa triggers the synthesis of N-methyl-1,4-diazabicyclo[2.2.2]octanium iodide, which co-crystallized with methanol (dabcoCH3I:2CH3OH, [C7H15N2]+I:2CH3OH). Structures of both solvates were determined by single-crystal X-ray diffraction. Compared to non-solvated dabcoHI governed by NH+⋯N hydrogen bonds, in the two methane solvates investigated there are NH⋯O, NHO, and OH⋯I hydrogen bonds, which illustrates the preference to replace the NH+⋯N hydrogen bonds with those involving oxygen atoms in high pressure.

Graphical abstract: Pressure induced transformations of 1,4-diazabicyclo[2.2.2]octane (dabco) hydroiodide: diprotonation of dabco, its N-methylation and co-crystallization with methanol

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Publication details

The article was received on 20 Jan 2010, accepted on 25 Mar 2010 and first published on 04 May 2010


Article type: Paper
DOI: 10.1039/C001379J
Citation: CrystEngComm, 2010,12, 2528-2532
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    Pressure induced transformations of 1,4-diazabicyclo[2.2.2]octane (dabco) hydroiodide: diprotonation of dabco, its N-methylation and co-crystallization with methanol

    A. Olejniczak and A. Katrusiak, CrystEngComm, 2010, 12, 2528
    DOI: 10.1039/C001379J

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