MadSci Network: Chemistry
Query:

Re: Structurally, why are some acids stronger than others?

Date: Tue Mar 7 08:11:02 2000
Posted By: Susan Rollinson, Organic chemistry, Alleghany Micro
Area of science: Chemistry
ID: 951586047.Ch
Message:

The most commonly used definition of an acid is a substance that can lose a proton (H+ ion):

HA <===> H+ + A-

Thus, anything that makes A- (the anion) a more stable chemical species will favor the right hand side of the equilibrium, and make HA a stronger acid.

There are two primary ways to help stabilize a negative charge:

  1. The inductive effects of strongly electronegative atoms (O, N, F, Cl) or groups (e.g. NO2), and
  2. resonance effects such as the COO- group. This matter is taken up in more depth in most organic chemistry textbooks-- check your library!

In your question, trifluoroacetic acid is a much stronger acid than acetic acid because the extremely electronegative fluorine atoms stabilize the negative charge on the trifluoroacetate anion relative to the acetate anion:

CF3COOH <===> H+ + CF3COO-
Ka = 5.9 x 10-1

CH3COOH <===> H+ + CH3COO-
Ka = 1.75 x 10-5

This discussion has ignored the effect of the solvent (usually water), polyprotic acids (capable of giving up more than one H+), and the conjugate acid of a base (e.g. NH4+). You can find out more about these topics in your textbook.


Current Queue | Current Queue for Chemistry | Chemistry archives

Try the links in the MadSci Library for more information on Chemistry.



MadSci Home | Information | Search | Random Knowledge Generator | MadSci Archives | Mad Library | MAD Labs | MAD FAQs | Ask a ? | Join Us! | Help Support MadSci


MadSci Network, webadmin@www.madsci.org
© 1995-2000. All rights reserved.