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Issue 23, 2003
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Self-organization of lactates in the gas phase

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Chiral recognition and subsequent selective self-organisation into hydrogen-bonded n-mers is observed in supersonic methyl lactate expansions. The νOH and νC[double bond, length as m-dash]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.

Graphical abstract: Self-organization of lactates in the gas phase

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Publication details

The article was received on 25 Jul 2003, accepted on 10 Oct 2003 and first published on 27 Oct 2003

Article type: Paper
DOI: 10.1039/B308580E
Citation: Org. Biomol. Chem., 2003,1, 4351-4358
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    Self-organization of lactates in the gas phase

    N. Borho and M. A. Suhm, Org. Biomol. Chem., 2003, 1, 4351
    DOI: 10.1039/B308580E

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