Knowledge Bank

Electronic structure calculations are reported for quinoline, 2,3-dimiethylquinoline, cyclobuta-B-quinoline, cyclopenta-B-quinoline and cyclobuta-G-quinoline, The fused rings perturb the calculated ionization potentials of the quinoline moiety. Analysis of the electronic wave function in terms of localized molecular orbitals elucidates the nature of these perturbations. Particular attention is paid to the influence of the fused ring on rehybridization of the nitrogen lone pair. The calculated ionization potentials will be correlated with experimentally measured ionization potentials (form PES spectra) and with measured basicities.