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Use of lanthanide shift reagents for the determination of the alkyl conformation in 2-alkyl-2-adamantanols

✍ Scribed by M. Hájek; P. Trška; L. Vodička; J. Hlavatý

Publisher: John Wiley and Sons
Year: 1977
Tongue: English
Weight: 407 KB
Volume: 10
Category: Article
ISSN: 0749-1581
DOI: 10.1002/mrc.1270100115

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✦ Synopsis

Abstract

The position of the lanthanide atom calculated from the pseudocontact shift equation was studied for 2‐adamantanol and 2‐methyl‐, 2‐ethyl‐, 2‐propyl‐, 2‐butyl‐2‐adamantanol. The possible methods of calculation considering rotation of the methyl group were ascertained in the case of 2‐methyl‐ and 2‐ethyl‐2‐adamantanol. It follows from these results that a 2‐alkyl group affects the effective position of the lanthanide atom. The conformational analysis of 2‐ethyl‐2‐adamantanol demonstrates a difference among conformations obtained with various shift reagents. A comparison with extended Huckel theory calculations shows that the shift reagent method can be used only for a qualitative determination of the most advantageous conformation of the ethyl group.

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