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Use of lanthanide shift reagents for the determination of the alkyl conformation in 2‐alkyl‐2‐adamantanols
Author(s) -
Hájek M.,
Trška P.,
Vodička L.,
Hlavatý J.
Publication year - 1977
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/mrc.1270100115
Subject(s) - reagent , chemistry , lanthanide , alkyl , atom (system on chip) , methyl group , group (periodic table) , medicinal chemistry , computational chemistry , stereochemistry , organic chemistry , ion , computer science , embedded system
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.