At the Experimental Limit of the NMR Conformational Analysis: 29 Si and 13 C NMR Study of the Conformational Equilibrium of 1-Phenyl-1- tert -butylsilacyclohexane

The low temperature (95 K) NMR study of 1-Ph-1- Bu-silacyclohexane ( ) showed the conformational equilibrium to be extremely one-sided toward thePh , -Bu conformer. The barrier to interconversion has been measured (4.2-4.6 kcal/mol) and the conformational equilibrium [Δν = 1990.64 ppm ( Si), 618.9 p...

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Bibliographic Details
Published in:Organic letters 2021-01, Vol.23 (2), p.405-409
Main Authors: Kleinpeter, Erich, Heydenreich, Matthias, Shainyan, Bagrat A
Format: Article
Language:English
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Summary:The low temperature (95 K) NMR study of 1-Ph-1- Bu-silacyclohexane ( ) showed the conformational equilibrium to be extremely one-sided toward thePh , -Bu conformer. The barrier to interconversion has been measured (4.2-4.6 kcal/mol) and the conformational equilibrium [Δν = 1990.64 ppm ( Si), 618.9 ppm ( C), -Ph : -Ph = (95.6-96.6%):(3.4-4.4%), = 25 ± 3, Δ ° = -  ln  = 0.58-0.63 kcal/mol] analyzed. The assignment and quantification of the NMR signals is supported by MP2 and DFT calculations.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03878