Stereodynamics of bond rotation in tertiary 1-naphthoic acid amides: A computational study

Computations sho that independent NCO 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 NCO, ArCO, and ethyl rotations. The calculated Gibbs energy barriers for these processes in solution are in good agreement with the experimental values. © 2005 Wiley Periodicals, Inc. J Comput Chem 26: 365–373, 2005