Organic & Biomolecular Chemistry 2003-12-07

Self-organization of lactates in the gas phase.

Nicole Borho, Martin A Suhm

Index: Org. Biomol. Chem. 1(23) , 4351-8, (2003)

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Abstract

Chiral recognition and subsequent selective self-organisation into hydrogen-bonded n-mers is observed in supersonic methyl lactate expansions. The nu(OH) and nu(C=O)-vibrations are investigated by ragout-jet FTIR-spectroscopy and lead to the assignment of homo- and heterochiral clusters of at least three different cluster sizes. Whereas homo- and heterochiral dimers are formed in similar amounts in the racemic mixture, prominent absorptions due to different homochiral and heterochiral lactate trimers and tetramers indicate highly specific chiral self-recognition beyond molecular pairs. Chemical modification of the ester-group (methyl-, ethyl- and isopropyl-lactate) and argon admixture to the helium expansion contribute importantly to an understanding of the cluster spectra and topology.