Vibrational Circular Dichroism in the CH Stretching Region of (+)-3(R)-Methylcyclohexanone and Chiral Deuteriated Isotopomers

Teresa B. Freedman, James Kallmerten, Elmer D. Lipp, Daryl A. Young, Laurence A. Nafie

Research output: Contribution to journalArticlepeer-review

11 Scopus citations


The CH stretching Raman, FTIR, and vibrational circular dichroism (VCD) spectra of 3(R)-methylcyclohexanone and its chiral 2, 2, 6, 6-d4, 4, 4-d2, 5, 5-d2and methyl-d3isotopomers, and the Raman and FTIR spectra of racemic 3-methylcyclohexanone-3-d1are presented and analyzed. Fourier self-deconvolution has been applied to the FTIR spectra to artificially enhance the resolution in order to determine individual band frequencies. Band assignments have been obtained on the basis of the spectral changes occurring due to selective deuteriation and from an analysis of the strong Fermi resonance interactions. The VCD spectral features of the five chiral isotopomers can all be understood in terms of the coupling of pairs of chirally oriented CH oscillators on adjacent carbon atoms and the removal of the degeneracy in the methyl modes.

Original languageEnglish (US)
Pages (from-to)689-698
Number of pages10
JournalJournal of the American Chemical Society
Issue number3
StatePublished - Feb 1988

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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