The rotational pathway of the phenyl ring in N, 3,3-trimethyl-2-phenyl-4-piperidone has been determined by molecular mechanics calculations to be chair piperidone ⇋ twist-boat piperidone ⇋ phenyl rotation. The calculated barrier height for the process (ca. 63 kJ/mol) is in good agreement with the previously reported experimental value of 54 kJ/mol in a remotely substituted phenyl derivative determined by 1H DNMR. © 1986, American Chemical Society. All rights reserved.
|Journal||Journal of Organic Chemistry|
|Publication status||Published - 1 Jan 1986|
Jaime, C., Rubiralta, M., Feliz, M., & Giralt, E. (1986). Molecular Mechanics Calculations on the C<inf>sp</inf>3-C<inf>sp</inf>2 Rotation in the N,3,3-Trimethyl-2-phenyl-4-piperidone System. Journal of Organic Chemistry, 51(21), 3951-3955. https://doi.org/10.1021/jo00371a007