Chiral recognition in jet-cooled complexes

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.