Abstract
Uracil and its derivatives have two carbonyl sites available for hydrogen-bond formation and the CO4 bond is considered as being more basic than the CO2 group. The proton affinity (PA) of the O4-atom has been measured experimentally by Mautner. In this work the proton affinity (PA) of the O2 atoms of uracil, thymine and 5-F uracil has been calculated from the ionization potential of the lone pair and the ionization energy of the 1 s electrons. The PA of the O4 and O2 atoms are correlated with the σ net density at these atoms. The difference between the PA of the two oxygen atoms allows the difference in their hydrogen bonding ability towards hydroxylic proton donors to be predicted. The predicted difference is about 1 kcal mol −1, which is in agreement with infrared and calorimetric results.
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