The conformational equilibrium free energy difference for the C-methyl group in N,3- and N,4-dimethylpiperidine, and therefore in 3- and 4-methylpiperidine to a good approximation, have been estimated to be 6.3 ± 0.3 and 8.3 ± 0.3 kJ mol–1 at 293 K in dodecane as solvent, using the ratios of diastereomeric ions formed by the kinetically controlled protonation of 13C isotopically enriched derivatives.
M. J. T. Robinson, J. Chem. Soc., Chem. Commun., 1975, 844 DOI: 10.1039/C39750000844
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