First, consider the general equation of a simple acid reaction:
The more stable the conjugate base, A-,
is then the more the equilibrium favours the product side.....
The more the equilibrium favours products, the more H+ there is....
The more H+ there is then the stonger H-A is as an acid....
So looking for factors that stabilize the conjugate base, A-, gives us a
Structure and pKa
The information here is to help you decide which structure of an acid
or base will dominate at a particular pH. Lets do a general case.
The equation for an acid is just HA = H+ + A- where = means equilibrium
pKa is defined as -log10 Ka where Ka = [H+][A-] / [HA].
From these expressions it is possible to derive the Henderson-Hasselbalch equation which is
pKa = pH + log [HA] / [A-]
This tells us that when the pH = pKa then log [HA] / [A-] = 0 therefore [HA] = [A-] ie equal amounts of the two forms.
If we make the solution more acidic, ie lower the pH, then pH < pKa and log [HA] / [A-] has to be > 0 so [HA] > [A-]. This makes sense as it tells us that the protonated form dominates in an acidic medium.
If instead we make the solution more basic, ie raise the pH, then pH > pKa and log [HA] / [A-] has to be < 0 so [HA] <[A-]. This makes sense as it tells us that the deprotonated form dominates in the basic medium.
These principles can be extended to poly acidic / basic systems (such as amino acids) by thinking of each pKa value in turn.
Let's look at an example.
To the right are the processes for the amino acid HISTIDINE, which has
three acidic groups of pKa's 1.82 (carboxylic acid) 6.04 (pyrrole NH) and
9.17 (ammonium NH). Histidine can exist in the four forms shown, depending
on the solution pH, from acidic pH (top) to basic pH. (bottom).
Starting from the top, we can imagine that as we add base, the most acidic proton is removed first (COOH), then the pyrrole NH then finally the amino NH. These take us through each of the forms in turn.
At pH < 1.82, A is the dominant form.
In the range 1.82 < pH < 6.02 B is the dominant form.
In the range 6.02 < pH < 9.17 C is the dominant form, and
when pH > 9.17, D is the major form in solution. OK?