Abstract
The rotational barrier around the N–C chiral axis in N-(2-tert-butylphenyl)-3,4-dihydrobenzoquinolin-2-one was found to be 6kcal/mol lower than that in N-(2-tert-butylphenyl)-3,4-dihydroquinolin-2-one. X-ray crystal structures and 1H NMR spectra of both compounds indicate that the significant decrease in the rotational barrier in benzoquinolinone is brought about by destabilization of the ground state which is highlighted by a considerable distortion of the N-C chiral axis.
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