Support by the DFG research training group GRK 782 and the Fonds der Chemischen Industrie is acknowledged. We are grateful to A. de Meijere for advice on nomenclature, U. Buck, C. Rice, and U. Schmitt for help and discussions, and A. Bochenkova for preliminary MP2 studies.
Chirality-Induced Switch in Hydrogen-Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase†
Article first published online: 3 MAY 2006
Copyright © 2006 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 45, Issue 21, pages 3440–3445, May 19, 2006
How to Cite
Adler, T. B., Borho, N., Reiher, M. and Suhm, M. A. (2006), Chirality-Induced Switch in Hydrogen-Bond Topology: Tetrameric Methyl Lactate Clusters in the Gas Phase. Angew. Chem. Int. Ed., 45: 3440–3445. doi: 10.1002/anie.200600380
- Issue published online: 10 MAY 2006
- Article first published online: 3 MAY 2006
- Manuscript Revised: 12 MAR 2006
- Manuscript Received: 29 JAN 2006
- hydrogen bonds;
- molecular recognition;
- vibrational spectroscopy
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).