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Issue 11, 2016
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Synthesis and the crystal structure of dimeric 1-hydroxyhexane-2,3-dione and the spectral characteristics of a model acireductone

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Abstract

An efficient synthetic route to 1-hydroxyhexane-2,3-dione, which is a tautomeric form of a model acireductone, is presented here. Interestingly, the compound was found to crystallise as a stable dimer, a molecule of which contains a 1,3-dioxolane ring. The dimer structure was solved using the PXRD (powder X-ray diffraction) method and confirmed by NMR, IR, and Raman spectroscopy and DFT calculations. The title compound dissolves in water with the formation of several monomeric forms of the model acireductone as revealed by UV-Vis and NMR spectra. The extinction coefficients of the neutral and anionic forms of the monomer were also determined.

Graphical abstract: Synthesis and the crystal structure of dimeric 1-hydroxyhexane-2,3-dione and the spectral characteristics of a model acireductone

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Publication details

The article was received on 19 Feb 2016, accepted on 06 Sep 2016 and first published on 07 Sep 2016


Article type: Paper
DOI: 10.1039/C6NJ00562D
Citation: New J. Chem., 2016,40, 9291-9303
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    Synthesis and the crystal structure of dimeric 1-hydroxyhexane-2,3-dione and the spectral characteristics of a model acireductone

    B. Trzewik, K. Chruszcz-Lipska, A. Miłaczewska, J. Opalińska-Piskorz, R. Karcz, R. Gryboś, M. Oszajca, K. Luberda-Durnaś, W. Łasocha, A. Fitch, B. Sulikowski and T. Borowski, New J. Chem., 2016, 40, 9291
    DOI: 10.1039/C6NJ00562D

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