A simple method for the determination of enantiomeric excess and identity of chiral carboxylic acids

Leo A. Joyce, Marc S. Maynor, Justin M. Dragna, Gabriella M. Da Cruz, Vincent M. Lynch, James W. Canary, Eric V. Anslyn

Research output: Contribution to journalArticlepeer-review

Abstract

The association between an achiral copper(II) host (1) and chiral carboxylate guests was studied using exciton-coupled circular dichroism (ECCD). Enantiomeric complexes were created upon binding of the enantiomers of the carboxylate guests to the host, and the sign of the resultant CD signal allowed for determination of the configuration of the studied guest. The difference in magnitudes and shapes of the CD signals, in conjunction with linear discriminant analysis (LDA), allowed for the identity of the guest to be determined successfully. A model was created for the host-guest complexes which successfully predicts the sign of the observed CD signal. Further, Taft parameters were used in the model, leading to rationalization of the observed magnitudes of the CD signals. Finally, the enantiomeric excess (ee) of unknown samples of three chiral carboxylic acid guests was determined with an average absolute error of ±3.0%.

Original languageEnglish (US)
Pages (from-to)13746-13752
Number of pages7
JournalJournal of the American Chemical Society
Volume133
Issue number34
DOIs
StatePublished - Aug 31 2011

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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