Issue 23, 2003
From the journal:

Organic & Biomolecular Chemistry

Self-organization of lactates in the gas phase

Nicole Borhoa  and  Martin A. Suhm*a  

* Corresponding authors

a Institut für Physikalische Chemie, Universität Göttingen, Tammannstr. 6, D-37077, Göttingen, Germany

Abstract

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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Article information

DOI
https://doi.org/10.1039/B308580E
Article type
Paper
Submitted
25 Jul 2003
Accepted
10 Oct 2003
First published
27 Oct 2003

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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