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NMR spectroscopic conformational analysis of 4‐methylene‐cyclohexyl pivalate—The effect of sp 2 hybridization
Author(s) -
Kleinpeter Erich,
Heydenreich Matthias,
Koch Andreas,
Krtitschka Angela,
Krüger Tobias,
Linker Torsten
Publication year - 2017
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.4630
Subject(s) - chemistry , methylene , conformational isomerism , moiety , nuclear magnetic resonance spectroscopy , ring (chemistry) , spectroscopy , stereochemistry , crystallography , dynamic equilibrium , molecule , medicinal chemistry , organic chemistry , physics , quantum mechanics
The conformational equilibrium of the axial/equatorial conformers of 4‐methylene‐cyclohexyl pivalate is studied by dynamic NMR spectroscopy in a methylene chloride/freon mixture. At 153 K, the ring interconversion gets slow on the nuclear magnetic resonance timescale, the conformational equilibrium (−ΔG°) can be examined, and the barrier to ring interconversion (ΔG # ) can be determined. The structural influence of sp 2 hybridization on both ΔG° and ΔG # of the cyclohexyl moiety can be quantified.