Abstract
Core-ionization energies of the hydroxy oxygen in phenol and p- and m-nitrophenol were measured using x-ray excitation. These energies were combined with experimental gas-phase acidities to give the initial- and final-state differences between these systems. Initial- and final-state shifts were also determined directly from electronic structure theory. These results indicate that the major factor in the higher acidity of p-nitrophenol relative to phenol is the initial-state charge distribution and not resonance delocalization in the anion (final-state effects). This result is in contrast to the current thinking of most organic chemists. Experimental results are also presented for m -nitrophenol. Ab initio theory is used to further elucidate the effects that contribute to the higher acidities of p- and m -nitrophenol relative to phenol.
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