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Institut des Sciences Moléculaires d'Orsay


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Accueil > Équipes scientifiques > Structure et dynamique des systèmes complexes isolés photoexcités (SYSIPHE) > CHIralité et spectroscoPIE (CHIPIE) > Role of weak molecular interactions in chiral recognition

Role of weak molecular interactions in chiral recognition

par Zehnacker-Rentien Anne - 17 novembre 2015 (modifié le 25 mars)

Ionic interactions are strong interactions and dominate in ionic complexes. Also, neutral complexes are often bound by "strong "hydrogen bonds like OH…O or OH..N interactions. However, weaker interactions like OH…π or CH…π as well as delocalised dispersion interactions play an important role in chiral recognition.

We have evidenced the role of weak interaction in neutral systems on the example of (1R,2S)-(+)-cis-1-amino-2-indanol and methyl lactate.

Structures for the (1R, 2S) - (+) - cis-1-amino-2-indanol complex and the R (left) and S (right) methyl lactate.
Structures for the (1R, 2S) - (+) - cis-1-amino-2-indanol complex and the R (left) and S (right) methyl lactate.

Dispersion plays an important role in the Napthyl ethanol-Methyl Lactate system and Methyl Mandelate-Methyl Lactate.

Even in ionic systems such as cinchona alkaloids dimers, where the main interaction is a strong hydrogen bond (almost a shared proton), weaker interactions play an important role for discriminating pseudo enantiomers.



Publications

How do Pseudoenantiomers Structurally Differ in the Gas Phase ? An IR/UV Spectroscopy Study of Jet‐Cooled Hydroquinine and Hydroquinidine
A. Sen, V. Lepere, K. Le Barbu‐Debus, and A. Zehnacker
ChemPhysChem, 2013, vol 14, 3559-3568

The role of weak hydrogen bonds in chiral recognition
D. Scuderi, K. Le Barbu-Debus, and A. Zehnacker
Phys. Chem. Chem. Phys. 2011, vol 13, 17916-179297

Chiral recognition in jet-cooled complexes of (1R,2S)-(+)-cis-1-amino-2-indanol and methyl lactate : on the importance of the CH⋯π interaction
K. Le Barbu-Debus, M. Broquier, A. Mahjoub, and A. Zehnacker-Rentien
Phys. Chem. Chem. Phys., 2009, vol 11, 7589-7598

Chiral Recognition between α-Hydroxylesters : A Double-Resonance IR/UV Study of the Complexes of Methyl Mandelate with Methyl Glycolate and Methyl Lactate
K. Le Barbu-Debus, M. Broquier, A. Mahjoub, and A. Zehnacker-Rentien
J. Phys. Chem. A, 2008, vol 112 (40), 9731–9741

Chiral recognition between lactic acid derivatives and an aromatic alcohol in a supersonic expansion : electronic and vibrational spectroscopy
N. Seurre, K. Le Barbu-Debus, F. Lahmani, A. Zehnacker, N. Borho, and M. A. Suhm
Phys. Chem. Chem. Phys., 2006, vol 8, 1007-1016

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