The conformational behaviour of free d -glucose—at last

The conformational behaviour of isolated d-glucose has been revealed in this work using Fourier transform microwave spectroscopy coupled with laser ablation of crystalline alpha - and beta -glucopyranose samples. Four conformers of alpha -d-glucopyranose and three of beta -d-glucopyranose have been...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2014-01, Vol.5 (2), p.515-522
Main Authors: Alonso, Jose L, Lozoya, Maria A, Pena, Isabel, Lopez, Juan C, Cabezas, Carlos, Mata, Santiago, Blanco, Susana
Format: Article
Language:English
Subjects:
Crystal structure
Fourier transforms
Hydrogen bonds
Laser ablation
Microwave spectroscopy
Networks
Rotational
Spectroscopy
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Summary:The conformational behaviour of isolated d-glucose has been revealed in this work using Fourier transform microwave spectroscopy coupled with laser ablation of crystalline alpha - and beta -glucopyranose samples. Four conformers of alpha -d-glucopyranose and three of beta -d-glucopyranose have been unequivocally identified on the basis of the spectroscopic rotational parameters in conjunction with ab initiopredictions. 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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c3sc52559g