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Issue 2, 2014
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The conformational behaviour of free D-glucose—at last

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Abstract

The conformational behaviour of isolated D-glucose has been revealed in this work using Fourier transform microwave spectroscopy coupled with laser ablation of crystalline α- and β-glucopyranose samples. Four conformers of α-D-glucopyranose and three of β-D-glucopyranose have been unequivocally identified on the basis of the spectroscopic rotational parameters in conjunction with ab initio predictions. Stereoelectronic hyperconjugative factors, like those associated with anomeric or gauche effects, as well as the cooperative OH⋯O chains extended along the entire molecule, are the main factors driving the conformational behaviour. The most abundant conformers exhibit a counter-clockwise arrangement (cc) of the network of intramolecular hydrogen bonds.

Graphical abstract: The conformational behaviour of free d-glucose—at last

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Publication details

The article was received on 11 Sep 2013, accepted on 15 Oct 2013 and first published on 16 Oct 2013


Article type: Edge Article
DOI: 10.1039/C3SC52559G
Chem. Sci., 2014,5, 515-522

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    The conformational behaviour of free D-glucose—at last

    J. L. Alonso, M. A. Lozoya, I. Peña, J. C. López, C. Cabezas, S. Mata and S. Blanco, Chem. Sci., 2014, 5, 515
    DOI: 10.1039/C3SC52559G

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