Chirality-Induced Switch in Hydrogen-Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase

Chirality-Induced Switch in Hydrogen-Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase

Supersonic jet expansions of racemic methyl lactate show a prominent OH‐stretching infrared absorption at 3401 cm−1 which is not present in the enantiopure compound. Experimental results and quantum chemical calculations show that the underlying tetrameric cluster has 2:2 stoichiometry of the R and...

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Veröffentlicht in:Angewandte Chemie International Edition 2006-05, Vol.45 (21), p.3440-3445
Hauptverfasser: Adler, Thomas B., Borho, Nicole, Reiher, Markus, Suhm, Martin A.
Format: Artikel
Sprache:eng
Schlagworte:
chirality
Cluster Analysis
Gases
Hydrogen Bonding
hydrogen bonds
Lactates - chemistry
Models, Molecular
molecular recognition
nanostructures
Polymers - chemistry
Spectrophotometry
vibrational spectroscopy
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Zusammenfassung:Supersonic jet expansions of racemic methyl lactate show a prominent OH‐stretching infrared absorption at 3401 cm−1 which is not present in the enantiopure compound. Experimental results and quantum chemical calculations show that the underlying tetrameric cluster has 2:2 stoichiometry of the R and S isomers and S4 symmetry (see picture; C orange, O red, H gray).
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200600380