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Thomas B. Adler, Nicole Borho, Markus Reiher and Martin A. Suhm Chirality-Induced Switch in Hydrogen-Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase Angewandte Chemie International Edition 45

Version of Record online: 3 MAY 2006 | DOI: 10.1002/anie.200600380

Thumbnail image of graphical abstract

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).

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