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Issue 19, 2012
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Identification and interconversion of diastereomeric oligo-Tröger bases probed by ion mobility mass spectrometry

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Abstract

Oligo-Tröger bases are auspicious scaffolds of molecular engineering, which motivates studies on the mechanism of their interconversion and on the facile determination of the relative configuration of their diastereoisomers. Protonated, sodiated, and argentated species of those compounds were therefore studied via ion-mobility mass spectrometry (IM-MS), allowing differentiation on the basis of the shapes of the ions. First, the isomerization was confirmed to be acid-catalyzed as it takes place readily in the case of protonated Tröger bases, whereas the metallated bases are configurationally stable. Second, the corrected arrival times of the various isomers of the cationized bases were found to show distinct differences in IM-MS, and their excellent correlation with the cross sections obtained from quantum chemical calculations paves the way toward the easy identification of diastereoisomers.

Graphical abstract: Identification and interconversion of diastereomeric oligo-Tröger bases probed by ion mobility mass spectrometry

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Publication details

The article was received on 23 Feb 2012, accepted on 28 Mar 2012 and first published on 28 Mar 2012


Article type: Paper
DOI: 10.1039/C2CP40585G
Citation: Phys. Chem. Chem. Phys., 2012,14, 6987-6995
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    Identification and interconversion of diastereomeric oligo-Tröger bases probed by ion mobility mass spectrometry

    Á. Révész, D. Schröder, T. A. Rokob, M. Havlík and B. Dolenský, Phys. Chem. Chem. Phys., 2012, 14, 6987
    DOI: 10.1039/C2CP40585G

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