| Autor: |
Yeoh SD; School of Chemistry and Bio-21 Institute, University of Melbourne, Parkville, Victoria 3010, Australia., Skene CE, White JM |
| Jazyk: |
angličtina |
| Zdroj: |
The Journal of organic chemistry [J Org Chem] 2013 Jan 18; Vol. 78 (2), pp. 311-9. Date of Electronic Publication: 2012 Dec 20. |
| DOI: |
10.1021/jo3020243 |
| Abstrakt: |
σ(C-C)-σ*(C-O) interactions involving the strained carbon-carbon bonds of α- and β-nopinol, and their ester and ether derivatives have been demonstrated in the solid state using the variable oxygen probe. These hyperconjugative interactions are manifested as a strong response of the C-OR bond distance to the electron demand of the OR substituent. Although the effects upon the donor C-C bond distances are not large enough to be measurable by X-ray crystallography, they do result in systematic and measurable effects on the (13)C-(13)C one-bond coupling constants. For the donor C-C bond, coupling constants decrease, consistent with weakening of this bond, while the intervening C-C bond coupling constants increase, consistent with bond strengthening, as the electron demand of OR increases. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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