Analytical Chemistry and Spectroscopy
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Carbon-13 NMR spectral data for a series of symmetrical 2,6-disubstituted adamantanes (O=, CH2=, CH3, OH, OCOCH3) are presented. The substituent effects on 13C chemical shifts are additive, except for carbons 2 and 6 in 2,6-adamantanedione. The non-additivity of the substituent effect in the diketone can be interpreted in terms of a through-space interaction of the carbonyl π-electrons; the additivity in the other derivatives indicates that there is no appreciable interaction between the substituents.
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