J.N. acknowlegdes funding by a Liebig Stipendium from the Fonds der Chemischen Industrie (FCI), and would like to thank Prof. M. Reiher for helpful discussions and generous support.
Induced Chirality in Achiral Media—How Theory Unravels Mysterious Solvent Effects†
Article first published online: 20 SEP 2007
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 46, Issue 41, pages 7738–7740, October 15, 2007
How to Cite
Neugebauer, J. (2007), Induced Chirality in Achiral Media—How Theory Unravels Mysterious Solvent Effects. Angew. Chem. Int. Ed., 46: 7738–7740. doi: 10.1002/anie.200702858
- Issue published online: 4 OCT 2007
- Article first published online: 20 SEP 2007
- Fonds der Chemischen Industrie (FCI)
- density functional calculations;
- solvent effects
The solvent makes the difference: Quantum chemical investigations show that chiroptical properties can originate mainly from a chiral solvent shell rather than from the chiral solute. By using this approach it is possible to explain, for example, why the optical rotation of (S)-methyloxirane is positive in water, but has a relatively strong negative value in benzene (see picture; red: (S)- or (R)-methyloxirane, blue benzene).