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AAT Bioquest

What are the factors that influence acidity?

Posted May 17, 2024


Answer

There are several factors which influence acidity. Two factors are atom size and charge delocalization. Larger atoms in E-H bonds weaken the bond, resulting in stronger acids. Moreover, increased charge delocalization with larger atoms stabilizes the conjugate base, making the acid stronger. Another factor is that the stability of an acid's conjugate base determines the acid's strength. Groups inducing polarization in E-H bonds stabilize the formed conjugate base, enhancing acidity. Additionally, acid strength is influenced by the strength of the bond to the ionizable hydrogen. A weakly bonded hydrogen ion is easier to remove, making the acid stronger. In contrast, strongly bonded hydrogen ions are more difficult to detach, resulting in weaker acids. Lastly, there are inductive effects involving the transfer of electrons by groups connected to an atom through bonds. Groups that withdraw electron density increase acidity by stabilizing the resulting negative charge upon ionization, while those that donate electrons decrease acidity.

Additional resources

A Summary of 1.24: A Summary of the Factors that Determine Acid Strength

Intracellular pH

Weak Acid pH Calculator

Weak Base pH Calculator