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

doi:10.1021/ja00211a005

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

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 language	English (US)
Pages (from-to)	689-698
Number of pages	10
Journal	Journal of the American Chemical Society
Volume	110
Issue number	3
DOIs	https://doi.org/10.1021/ja00211a005
State	Published - Feb 1988

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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

abstract = "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.",

author = "Freedman, {Teresa B.} and James Kallmerten and Lipp, {Elmer D.} and Young, {Daryl A.} and Nafie, {Laurence A.}",

year = "1988",

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doi = "10.1021/ja00211a005",

language = "English (US)",

volume = "110",

pages = "689--698",

journal = "Journal of the American Chemical Society",

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publisher = "American Chemical Society",

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T1 - Vibrational Circular Dichroism in the CH Stretching Region of (+)-3(R)-Methylcyclohexanone and Chiral Deuteriated Isotopomers

AU - Freedman, Teresa B.

AU - Kallmerten, James

AU - Lipp, Elmer D.

AU - Young, Daryl A.

AU - Nafie, Laurence A.

PY - 1988/2

Y1 - 1988/2

N2 - 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.

AB - 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.

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

Abstract

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