An AM1 calculational study of the protonation and reactions of 3,4-dihydro-2-oxo-1,4-ethanoquinoline, 3,4-dihydro-2-oxo-1,4-propanoquinoline, 3,3,4,5-tetrahydro-2-oxo-1,5-ethanobenzazepine, 3,3,4,5-tetrahydro-2-oxo-1,5-propanobenzazepine, and N-methyl-4-bromo-2-methylacetanilide

The gas phase N- and O-protonation of distorted amides 3,4-dihydro-2-oxo-1,4-ethanoquinoline (1a), 3,4-dihydro-2-oxo-1,4-propanoquinoline (1b), 3,3,4,5-tetrahydro-2-oxo-1,5-ethanobenzazepine (1c), and 3,3,4,5-tetrahydro-2-oxo-1,5-propanobenzazepine (1d) and normal amides 4-bromo-2,N-dimethylacetanilide (5a) and 2,N-dimethylacetanilide (5b), along with the N-protonation of benzoquinuclidine (7), has been studied calculationally at the …