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17O, 13C and 1H NMR and IR spectral study of crowded ketones: possible intramolecular C—H···O interactions

✍ Scribed by Xu-rong Qin; Yasuko Ishizuka; John S. Lomas; Takahiro Tezuka; Hiroshi Nakanishi

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
101 KB
Volume
40
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Unusual behaviour was observed in the study of the ^17^O, ^13^C and ^1^H NMR and IR spectra of crowded (1‐adamantyl)alkyl ketones. As the size of the alkyl substituent is increased, abnormal upfield chemical shifts in the ^13^C NMR and downfield shifts in the ^17^O NMR of the carbonyl group, as well as downfield shifts in the ^1^H NMR of the adamantyl γ'‐protons, are found. In the IR spectrum, the ν~CO~ stretching frequencies of the ketones with bulky substituents show considerable red shifts. Correlation of the NMR shifts with the number of γ‐carbon atoms of the alkyl substituents and comparison with the IR results indicated that there is an intramolecular through‐space CH···O interaction in crowded ketones. This was supported by the results of ab initio calculations. Copyright © 2002 John Wiley & Sons, Ltd.

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