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DiLabio GA, Ingold KU, Roydhouse MD, et al. Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study. Org Lett. 2004;6(23):4319-22doi: 10.1021/ol0481683.
DiLabio, G. A., Ingold, K. U., Roydhouse, M. D., & Walton, J. C. (2004). Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study. Organic letters, 6(23), 4319-22. https://doi.org/10.1021/ol0481683
DiLabio, Gino A, et al. "Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study." Organic letters vol. 6,23 (2004): 4319-22. doi: https://doi.org/10.1021/ol0481683
DiLabio GA, Ingold KU, Roydhouse MD, Walton JC. Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study. Org Lett. 2004 Nov 11;6(23):4319-22. doi: 10.1021/ol0481683. PMID: 15524473.
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Org Lett. 2004 Nov 11;6(23):4319-22. doi: 10.1021/ol0481683.

Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals. An experimental and theoretical study.

Organic letters

Gino A DiLabio, Keith U Ingold, Mark D Roydhouse, John C Walton

Affiliations

  1. National Institute for Nanotechnology, National Research Council of Canada, W6-010 ECERF, 9107 116th Street, Edmonton, AB, Canada T6G 2V4.

PMID: 15524473 DOI: 10.1021/ol0481683

Abstract

Axial and equatorial cyclohexylacyl and tetrahydropyranyl-2-acyl radicals gave distinct EPR spectra thanks to surprisingly large beta-hydrogen atom hyperfine splittings that enabled them to be characterized and monitored. DFT computations indicated that the axial species (X = CH(2)) had a higher barrier to rotation about the (O)C(alpha)-C(beta) bond. The computed difference Delta H degrees for the axial and equatorial radicals (R = H, X = CH(2)) was 0.8 kcal mol(-)(1).

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