Stereodynamics of bond rotation in tertiary 1-naphthoic acid amides: a computational study.
Computations sho that independent N-CO rotation is not possible in N,N-diethyl-1-naphthamide, and that the coalescence signal corresponding to methyl equivalence observed in the VT NMR spectrum of this system is caused by a complex process whose rate-determining step implies concerted N-CO, Ar-CO, and ethyl rotations. The calculated Gibbs energy barriers for these processes in solution are in good agreement with the experimental values.
Campomanes
Pablo
P
Departamento de Química Física y Analítica, Facultad de Química, Universidad de Oviedo, C/Julián Clavería 8, 33006 Oviedo, Principado de Asturias, Spain.
Menéndez
M Isabel
MI
López
Ramón
R
Sordo
Tomás L
TL