We report the first adiabatic ionization energy ( I 1 ) of benzene, and the ortho, meta and para isomers of fluoro-, chloro- and bromobenzonitrile, extracted from gas-phase photoionization spectra measured up to the LiF cut-off. In every case, I 1 for the disubstituted benzene species is blue-shifted from I 1 in benzene. Moreover, I 1 decreases along the series F, Cl, Br. We explain these trends qualitatively by invoking destabilization/stabilization of the topmost filled π MO of benzene by donor/acceptor substituents.
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Findley et al. (1987) studied this question.
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