Open AccessMolecular Recognition in Glycolaldehyde, the Simplest Sugar: Two Isolated Hydrogen Bonds Win Over One Cooperative Pair
Author(s) -
Altnöder Jonas,
Lee Juhyon J.,
Otto Katharina E.,
Suhm Martin A.
Publication year - 2012
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201200031
Subject(s) - glycolaldehyde , hydrogen bond , chemistry , dimer , intramolecular force , intermolecular force , molecular recognition , infrared spectroscopy , computational chemistry , photochemistry , chemical physics , stereochemistry , molecule , organic chemistry , catalysis
Carbohydrates are used in nature as molecular recognition tools. Understanding their conformational behavior upon aggregation helps in rationalizing the way in which cells and bacteria use sugars to communicate. Here, the simplest α ‐hydroxy carbonyl compound, glycolaldehyde, was used as a model system. It was shown to form compact polar C 2 ‐symmetric dimers with intermolecular OH⋅⋅⋅OC bonds, while sacrificing the corresponding intramolecular hydrogen bonds. Supersonic jet infrared (IR) and Raman spectra combined with high‐level quantum chemical calculations provide a consistent picture for the preference over more typical hydrogen bond insertion and addition patterns. Experimental evidence for at least one metastable dimer is presented. A rotational spectroscopy investigation of these dimers is encouraged, also in view of astrophysical searches. The binding motif competition of aldehydic sugars might play a role in chirality recognition phenomena of more complex derivatives in the gas phase.