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Analysis of the Electronic Factors Controlling the N1s and the First two π (a2, b1) Photoelectron Ionizations in N-Containing Monosubstituted Benzenes (Ph-NRR′ and Ph-N=X)

The first two π(a2, b1) IE’s, of monosubstituted benzenes containing di- and tri-coordinated nitrogen directly linked to the ring have been measured and analysed together with the N1s IE. These photoelectron properties are found to respond in the same sense, though to different extents, to inductive and mesomeric interactions that the N-containing substituents sustain with the aromatic ring. The different sensitivities of these properties to substituent changes are discussed in connection with mechanisms of transmission of electronic effects with the aid of the ground state electronic structures determined by means of ab-initio calculations. The relative contribution of the relaxation energy to the considered core and valence IE’s is also examined by referring to the model used by Gelius and Siegbahn. The factors determining the apparently anomalous behaviour of nitrobenzene are discussed