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

Ágnes Révész, Detlef Schröder, T. Rokob, Martin Havlík, Bohumil Dolenský

Research output: Contribution to journalArticle

10 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)6987-6995
Number of pages9
JournalPhysical Chemistry Chemical Physics
Volume14
Issue number19
DOIs
Publication statusPublished - May 21 2012

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Mass spectrometry
mass spectroscopy
Ions
ions
Isomerization
Scaffolds
Isomers
isomerization
arrivals
isomers
engineering
acids
Acids
cross sections
configurations

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Physics and Astronomy(all)

Cite this

Identification and interconversion of diastereomeric oligo-Tröger bases probed by ion mobility mass spectrometry. / Révész, Ágnes; Schröder, Detlef; Rokob, T.; Havlík, Martin; Dolenský, Bohumil.

In: Physical Chemistry Chemical Physics, Vol. 14, No. 19, 21.05.2012, p. 6987-6995.

Research output: Contribution to journalArticle

Révész, Ágnes ; Schröder, Detlef ; Rokob, T. ; Havlík, Martin ; Dolenský, Bohumil. / Identification and interconversion of diastereomeric oligo-Tröger bases probed by ion mobility mass spectrometry. In: Physical Chemistry Chemical Physics. 2012 ; Vol. 14, No. 19. pp. 6987-6995.
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