Chiral recognition between alpha-hydroxylesters: a double-resonance IR/UV study of the complexes of methyl mandelate with methyl glycolate and methyl lactate

Chiral recognition between alpha hydroxylesters has been studied in jet-cooled complexes of methyl mandelate with methyl lactate. The complex with nonchiral methyl glycolate has also been studied for the sake of comparison. The hydrogen-bond topology of the complexes has been interrogated by means of IR/UV double-resonance spectroscopy in the range of 3 mum. A theoretical approach has been conducted in conjunction with the experimental work to assist in the analysis of the spectra. Owing to the conformational flexibility of the subunits at play, emphasis has been put on the methodology used for the exploration of the potential-energy surface. The hydrogen-bond topology is very similar in the homo- and heterochiral complexes. It involves insertion of the hydroxyl group of methyl mandelate within the intramolecular hydrogen bond of methyl lactate or methyl glycolate, resulting in a five-membered ring. This contrasts with methyl lactate clusters previously studied by FTIR spectroscopy in a filet jet.