pKa Scale

Definition of pKa

You can think of any molecule that has a proton on it as being an acid.  They don't have to be very strong acids, but nonetheless they can behave as an acid.

If you take some arbitrary acid, H-A, and place it in a solvent usually water) it will undergo an acid base dissociation reaction as follows.  An equilibrium constant Ka can be written for this equilibrium.  A strong acid would have a large Ka.  This indicates the proton (H+) is not tiightly bound.  While a weak acid would have a very small Ka.  

Now recall from general chemistry the definition of pH = -log([H+]). We define pKa the same way.

       pKa = -log(Ka)

This have been done and tabulated for many thousands of compounds.  Lets think about this equation for a minute.  Suppose you had a very strong acid.  The equilibrium above would be far to the right.  The equilibrium constant would be very large and log(Ka) would be very large.  However the -log(Ka) would be very small.

Take NoteTherefore a strong acids have low pKa's.  Note this goes in the same direction as pH.  A solution with a low pH is acidic and a molecule with a low pKa is acidic as well.

 

Chemists have done this for many compounds.  Below is a small subset with which you should be familair (i.e. memorize).

Table of pKa's

Acid

Conjugate Base

pKa

HI

I-

-10

H2SO4

HSO4-

-9

HCl

Cl-

-4

RCO2H

RCO2-

4 to 6

RNH3+

RNH2

10 to 12

H2O

OH-

15.7

ROH

RO-

16 to 18

RC≡CH (alkyne)

RC≡C-

26

NH3

NH2-

36

RNH2

RNH-

36

R2C=CH2 (alkene)

R2C=CH-

45

RH (alkane)

R-

60