One critical factor in determining the strength of acids can be
the strength of the HA bond. Clearly if the proton is very
tightly held by the rest of the molecule, it will require a lot
of energy to remove it, and hence the acid will be weak. Equally,
a weakly-held proton is a characteristic of a strong acid.
The above equilibria illustrate the point. CH5+
(which can be made, and is used in the gas phase to protonate virtually
anything, as a very strong acid) does not have a particularly strong
bond to the proton. However, all of the CH bond in methane
are much stronger, and hence more difficult to break. Thus
methane itself is a very weak acid.
Obviously, to present these as the only considerations
is misleading, as there are other factors such as the relative stabilities
of acid and conjugate base.
Consideration of the HA bond strength alone is rarely
useful. It does make sense, however in certain instances,
such as the halogen acids: HF, HCl, HBr, HI (although even here
it is not the only factor), as the acid strengths increase with
decreasing bond strength.
| Acid |
Bond Strength (kJmol-1) |
pKa |
| HI |
299 |
-11 |
| HBr |
366 |
-9 |
| HCl |
431 |
-7 |
| HF |
565 |
3.5 |
The other main factor involved here is the better
charge distribution on the larger anions.
|