Conformational Flexibility in Hydrated Sugars:  the Glycolaldehyde−Water Complex

Conformational flexibility in the smallest hydrated sugar, the glycolaldehyde−water complex, has been investigated in the gas phase by means of a combination of a microwave Fourier transform spectroscopy experiment in a supersonic molecular beam and ab initio quantum chemistry calculations. The wate...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2006-08, Vol.128 (32), p.10467-10473
Main Authors: Aviles-Moreno, Juan-Ramon, Demaison, Jean, Huet, Thérèse R
Format: Article
Language:English
Subjects:
Acetaldehyde - analogs & derivatives
Acetaldehyde - chemistry
Acetaldehyde - metabolism
Atmospheric and Oceanic Physics
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Chemical Physics
Chemical Sciences
Chemistry
Exact sciences and technology
Gases - chemistry
General and physical chemistry
Models, Chemical
Molecular Conformation
or physical chemistry
Organic chemistry
Physics
Preparations and properties
Quantum Physics
Quantum Theory
Spectroscopy, Fourier Transform Infrared
Theoretical and
Water - chemistry
Water - metabolism
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Summary:Conformational flexibility in the smallest hydrated sugar, the glycolaldehyde−water complex, has been investigated in the gas phase by means of a combination of a microwave Fourier transform spectroscopy experiment in a supersonic molecular beam and ab initio quantum chemistry calculations. The water molecule inserts into glycolaldehyde using H-bonding selectivity:  the two lowest energy conformations are stabilized by two intermolecular hydrogen bonds, and the next two by one intra- plus one intermolecular hydrogen bond. A dynamical flexibility associated with the two lowest energy conformations has been experimentally observed and accurately modeled with a two-dimensional potential energy surface involving the hydroxyl group and the free OH water group coordinates. The conclusions drawn from the role played in the conformational flexibility by the hydroxyl and carbonyl groups are extended to other carbohydrates and biomolecules.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja062312t