Chirality sensing by nonchiral porphines

Jan Labuta, Shinsuke Ishihara, Atsuomi Shundo, Satoshi Arai, Shinji Takeoka, Katsuhiko Ariga, Jonathan P. Hill

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28 Citations (Scopus)

Abstract

Let's split the difference: Nonchiral porphine macrocycles have been used as chemical shift agents for the determination of the enantiomeric excesses of chiral carboxylic acids. This method is based on the observation of the relative splitting induced in the 1H NMR resonances of the porphine protons. A mechanism for the recognition based on the fast exchange of the guest molecules has been proposed (see scheme).

Original languageEnglish
Pages (from-to)3558-3561
Number of pages4
JournalChemistry - A European Journal
Volume17
Issue number13
DOIs
Publication statusPublished - 2011 Mar 21

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Keywords

  • carboxylic acids
  • chiral solvating agents
  • enantiomeric excess
  • NMR spectroscopy
  • porphyrinoids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Labuta, J., Ishihara, S., Shundo, A., Arai, S., Takeoka, S., Ariga, K., & Hill, J. P. (2011). Chirality sensing by nonchiral porphines. Chemistry - A European Journal, 17(13), 3558-3561. https://doi.org/10.1002/chem.201100052