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Molecular Recognition in Glycolaldehyde, the Simplest Sugar: Two Isolated Hydrogen Bonds Win Over One Cooperative Pair

dc.contributor.authorAltnöder, Jonas
dc.contributor.authorLee, Juhyon J.
dc.contributor.authorOtto, Katharina E.
dc.contributor.authorSuhm, Martin A.
dc.date.accessioned2012-11-29T09:05:43Z
dc.date.available2012-11-29T09:05:43Z
dc.date.issued2012
dc.relation.ISSN2191-1363
dc.identifier.urihttp://resolver.sub.uni-goettingen.de/purl?gs-1/8370
dc.description.abstractCarbohydrates 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 a-hydroxy carbonyl compound, glycolaldehyde, was used as a model system. It was shown to form compact polar C2-symmetric dimers with intermolecular O H···O=C 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.
dc.description.sponsorshipOpen-Access-Publikationsfonds 2012
dc.language.isoeng
dc.rightsopenAccess
dc.rights.urihttp://creativecommons.org/licenses/by-nc/3.0/
dc.subjectab initio calculations; carbohydrates; conformational analysis; infrared spectroscopy; molecular recognition; Raman spectroscopy
dc.titleMolecular Recognition in Glycolaldehyde, the Simplest Sugar: Two Isolated Hydrogen Bonds Win Over One Cooperative Pair
dc.typejournalArticle
dc.identifier.doi10.1002/open.201200031
dc.type.versionpublishedVersion
dc.bibliographicCitation.volume1
dc.bibliographicCitation.issue6
dc.bibliographicCitation.firstPage269
dc.bibliographicCitation.lastPage275
dc.type.subtypejournalArticle
dc.description.statuspeerReviewed
dc.bibliographicCitation.journalChemistryOpen


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