FT ICR investigations of chiral supramolecular propellers of dialkyltartrate trimers with methylammonium ions

E. V. Denisov, V. Shustryakov, E. N. Nikolaev, F. J. Winkler, R. Medina

Research output: Contribution to journalArticlepeer-review

18 Citations (Scopus)

Abstract

Fourier transform ICR mass spectrometry has been applied to study the gas-phase association of chiral dialkyltartrates M with methylammonium and ammonium ions A. The method uses enantiomer-labeled racemates of dimethyl-(S)- and [2H6]dimethyl-(R)-tartrates (s and r) and diisopropyl-(S)- and [2H14]diisopropyl-(R)-tartrates (S and R). Abundant trimer adduct clusters M3·AH+ could be produced in the ICR cell at temperatures of 20-25°C. The diastereomeric clusters sss·AH+, ssr·AH+, srr·AH+ and rrr·AH+ did not show the statistical abundances 1:3:3:1, but a pattern near 15:1:1:15 (and near 10:1:1:10 for the diisopropyl homologs). These chiral discriminations are much higher than previous effects under CI conditions. The kinetics of the cluster formation has been studied. Semi-empirical AM1 and PM3 calculations of clusters M3·AH+ are reported.

Original languageEnglish
Pages (from-to)259-268
Number of pages10
JournalInternational Journal of Mass Spectrometry and Ion Processes
Volume167-168
DOIs
Publication statusPublished - 1997
Externally publishedYes

Keywords

  • AM1 and PM3 calculations
  • Chiral recognition
  • Fourier transform ICR
  • Proton-bound clusters
  • Supramolecular structures

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