Chiral Recognition in Jet-Cooled Complexes

Nathalie Seurre; Katia Le Barbu-Debus; Françoise Lahmani; Nicole Borho; Martin A. Suhm; Anne Zehnacker

doi:10.1071/CH04120

RESEARCH ARTICLE

Chiral Recognition in Jet-Cooled Complexes

Nathalie Seurre ^A , Katia Le Barbu-Debus ^A , Françoise Lahmani ^A , Nicole Borho ^B , Martin A. Suhm ^B and Anne Zehnacker ^A ^C

+ Author Affiliations

- Author Affiliations

^A Laboratoire de Photophysique Moléculaire du CNRS, Université Paris XI, 91405 Orsay Cédex, France.

^B Institut für Physikalische Chemie, Universität Göttingen, 37077, Göttingen, Germany.

^C Corresponding author. Email: anne.zehnacker@ppm.u-psud.fr

Australian Journal of Chemistry 57(12) 1149-1152 https://doi.org/10.1071/CH04120
Submitted: 5 May 2004 Accepted: 14 September 2004 Published: 8 December 2004

Abstract

Jet-cooled complexes formed between a chiral probe [(±)-2-naphthyl-1-ethanol] and chiral bifunctional partners that show an intramolecular hydrogen bond have been studied by laser-induced fluorescence and IR fluorescence-dip spectroscopy as well as with DFT calculations. Chiral discrimination results in a chirality-dependent competition between the intramolecular and the intermolecular hydrogen bonds. In the case of (±)-methyl lactate, this competition manifests itself in the size of the formed adducts. In particular, while 1 : 1 complexes are the most abundant species observed when (R)-2-naphthyl-1-ethanol is mixed with (S)-methyl lactate, they are absent in the case of the SS mixture, which only forms 1 : 2 adducts.

References

Chiral Recognition in Jet-Cooled Complexes

Abstract

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