Disentangling the Puzzle of Hydrogen Bonding in Vitamin C

Fast-passage Fourier transform microwave spectroscopy in combination with a laser ablation source has been successfully applied to probe vitamin C (l-ascorbic acid) in the gas phase. Its ethyldiol side chain and two hydroxyl groups around the γ-lactone ring provide five internal rotation axes, enabl...

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Bibliographic Details
Published in:The journal of physical chemistry letters 2013-01, Vol.4 (1), p.65-69
Main Authors: Peña, Isabel, Daly, Adam M, Cabezas, Carlos, Mata, Santiago, Bermúdez, Celina, Niño, Amaya, López, Juan C, Grabow, Jens-Uwe, Alonso, José L
Format: Article
Language:English
Subjects:
Spectroscopy, Photochemistry, and Excited States
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Summary:Fast-passage Fourier transform microwave spectroscopy in combination with a laser ablation source has been successfully applied to probe vitamin C (l-ascorbic acid) in the gas phase. Its ethyldiol side chain and two hydroxyl groups around the γ-lactone ring provide five internal rotation axes, enabling vitamin C to assume a wide variety of nonplanar 3D cooperative hydrogen bond networks that can also include the keto and ether functions. The rotational constants extracted from the analysis of the spectrum unequivocally identify the existence of three dominant conformers stabilized by different intramolecular hydrogen bonding motifs forming five-, six-, or seven-membered rings.
ISSN:1948-7185
1948-7185
DOI:10.1021/jz301947g