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Deshielding γ–gaucheeffects in 13C magnetic resonance: a comparison of the conformational behaviour of the acetyl group in cyclohexane and 5-substituted-1,3-dioxane systems

Authors :
Buchanan, G. W.
Preusser, S. H.
Webb, V. L.
Source :
Canadian Journal of Chemistry; July 1984, Vol. 62 Issue: 7 p1308-1311, 4p
Publication Year :
1984

Abstract

Low temperature (173 K) 13C spectra of acetylcyclohexane, 1-acetyl-1-methylcyclohexane, and 5-acetyl-5-methyl-1,3-dioxane are reported. Data permit the first direct measurement of −ΔG0for the acetyl group bonded to cyclohexane. The value obtained, 1.02 ± 0.05 kcal/mol in CS2–CD2Cl2solution, is considerably lower than that determined by equilibration methods. Factors contributing to observed axial–equatorial carbonyl carbon chemical shift differences for substituted cyclohexanes and 1,3-dioxanes are discussed.

Details

Language :
English
ISSN :
00084042 and 14803291
Volume :
62
Issue :
7
Database :
Supplemental Index
Journal :
Canadian Journal of Chemistry
Publication Type :
Periodical
Accession number :
ejs19689439
Full Text :
https://doi.org/10.1139/v84-219