Investigation of mandelic acid bonding on Pirkle type chromatographic stationary phases by Raman spectroscopy

E. Horváth, J. Kristóf, R. L. Frost, L. Rintoul, A. Rédey, W. Forsling

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The bonding of mandelic acid enantiomers has been studied on benzene-leucine, dinitrobenzene-leucine and dinitrobenzene-phenylalanine type chiral stationary phases connected to zeolite A supports. The π-donor, π-acceptor and H-bonding interactions responsible for diastereomer pair formations can be studied under quasi in situ chromatographic conditions by Fourier transform Raman and surface enhanced Raman spectroscopic techniques. Structural differences between diastereomer pairs result in observable spectral differences at a phase load of approx. 50%. It was shown that the decreasing π-acceptor character of the phase is associated with its increasing capability of H-bond formation. Correlating spectral data to chromatographic results it can be concluded that, in addition to H-bonding as well as to π-donor-π-acceptor interactions, steric hindrances due to bulky moieties of either the stationary phase or the analyte molecules are of importance in successful separations. Copyright (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)37-46
Number of pages10
JournalJournal of Chromatography A
Volume893
Issue number1
DOIs
Publication statusPublished - Sep 29 2000

Fingerprint

Dinitrobenzenes
Raman Spectrum Analysis
Leucine
Raman spectroscopy
Zeolites
Fourier Analysis
Benzene
Phenylalanine
Enantiomers
Fourier transforms
Molecules
mandelic acid

Keywords

  • Chiral stationary phases, LC
  • Enantiomer bonding
  • Mandelic acid
  • Raman spectroscopy

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

Investigation of mandelic acid bonding on Pirkle type chromatographic stationary phases by Raman spectroscopy. / Horváth, E.; Kristóf, J.; Frost, R. L.; Rintoul, L.; Rédey, A.; Forsling, W.

In: Journal of Chromatography A, Vol. 893, No. 1, 29.09.2000, p. 37-46.

Research output: Contribution to journalArticle

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AU - Frost, R. L.

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AU - Rédey, A.

AU - Forsling, W.

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AB - The bonding of mandelic acid enantiomers has been studied on benzene-leucine, dinitrobenzene-leucine and dinitrobenzene-phenylalanine type chiral stationary phases connected to zeolite A supports. The π-donor, π-acceptor and H-bonding interactions responsible for diastereomer pair formations can be studied under quasi in situ chromatographic conditions by Fourier transform Raman and surface enhanced Raman spectroscopic techniques. Structural differences between diastereomer pairs result in observable spectral differences at a phase load of approx. 50%. It was shown that the decreasing π-acceptor character of the phase is associated with its increasing capability of H-bond formation. Correlating spectral data to chromatographic results it can be concluded that, in addition to H-bonding as well as to π-donor-π-acceptor interactions, steric hindrances due to bulky moieties of either the stationary phase or the analyte molecules are of importance in successful separations. Copyright (C) 2000 Elsevier Science B.V.

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