Acid-neutralizing capacity, definition

Treatment of buffer efficiency in general is not limited to examination of various monoprotic and polyprotic acids, but rather to the behavior of mixtures of acids. Further, from plots of buffer index vs. pH, it is easy to see that strong acids and bases are reasonable buffers for the extreme (low and high) Ph ranges. This leads to the definition of a buffer as a solution that has neutralization capacity, rather the more limited but commonly used definition as a mixture of a weak acid and its conjugate base (See Figure 8.5). 

According to the Brpnsted definition, the acidity of a molecule is associated with its capacity to give up a proton Ph—NH2 — Ph—NH +H+. The change of standard enthalpy or free energy of this deprotonation reaction is a measure of the intrinsic acidity. As discussed above, in solution, the propensity of an aniline derivative is to accept a proton. The measured dissociation constant (pATa) is related to the basicity of the neutral molecule (or the acidity of the anilinium cations). As a consequence, relatively little is known about their acidity and/or the anilinide anions. However, the NH acidities have been well established in hydroxamic acids even though the latter usually behave as O-acids134. It is therefore of interest to get some insight into the deprotonation of aniline in the gas phase. 

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