Conjugate acid

A conjugate acid, within the Brønsted–Lowry acid–base theory, is a chemical compound formed by the
reception of a proton (H+) by a base—in other words, it is a base with a hydrogen ion added to it, as in the
reverse reaction it loses a hydrogen ion. On the other hand, a conjugate base is what is left over after an acid
has donated a proton during a chemical reaction. Hence, a conjugate base is a species formed by the removal
of a proton from an acid, as in the reverse reaction it is able to gain a hydrogen ion.[1] Because some acids are
capable of releasing multiple protons, the conjugate base of an acid may itself be acidic.

In summary, this can be represented as the following chemical reaction:

Acid + Base ⇌ Conjugate Base + Conjugate Acid

Johannes Nicolaus Brønsted and Martin Lowry

introduced the Brønsted–Lowry theory, which
proposed that any compound that can transfer a
proton to any other compound is an acid, and the
compound that accepts the proton is a base. A
proton is a nuclear particle with a unit positive
electrical charge; it is represented by the symbol
H+ because it constitutes the nucleus of a
Johannes Nicolaus Brønsted (left) and Martin Lowry (right).
hydrogen atom,[2] that is, a hydrogen cation.

A cation can be a conjugate acid, and an anion

can be a conjugate base, depending on which substance is involved and which acid–base theory is the
viewpoint. The simplest anion which can be a conjugate base is the solvated electron whose conjugate acid is
the atomic hydrogen.

Contents
Acid-base reactions
Strength of conjugates
Identifying conjugate acid-base pairs
Applications
Table of acids and their conjugate bases
Table of bases and their conjugate acids
See also
References
External links

Acid-base reactions
In an acid-base reaction, an acid plus a base reacts to form a conjugate base plus a conjugate acid:
Conjugates are formed when an acid loses a hydrogen proton or a base gains a hydrogen proton. Refer to the
following figure:

We say that the water molecule is the conjugate acid of the hydroxide ion after the latter received the hydrogen
proton donated by ammonium. On the other hand, ammonia is the conjugate base for the acid ammonium after
ammonium has donated a hydrogen ion towards the production of the water molecule. We can also refer to
OH- as a conjugate base of H2 O, since the water molecule donates a proton towards the production of NH+4 in
the reverse reaction, which is the predominating process in nature due to the strength of the base NH3 over the
hydroxide ion. Based on this information, it is clear that the terms "Acid", "Base", "conjugate acid", and
"conjugate base" are not fixed for a certain chemical species; but are interchangeable according to the reaction
taking place.

Strength of conjugates
The strength of a conjugate acid is directly proportional to its dissociation constant. If a conjugate acid is
strong, its dissociation will have a higher equilibrium constant and the products of the reaction will be favored.
The strength of a conjugate base can be seen as the tendency of the species to "pull" hydrogen protons
towards itself. If a conjugate base is classified as strong, it will "hold on" to the hydrogen proton when in
solution and its acid will not dissociate.

If a species is classified as a strong acid, its conjugate base will be weak.[3] An example of this case would be
the dissociation of Hydrochloric acid HCl in water. Since HCl is a strong acid (it dissociates to a great extent),
− +
its conjugate base (Cl ) will be a weak conjugate base. Therefore, in this system, most H will be in the form
+
of a Hydronium ion H3 O instead of attached to a Cl anion and the conjugate base will be weaker than a
water molecule.

On the other hand, if a species is classified as a weak acid its conjugate base will not necessarily be a strong
base. Consider that acetate, the conjugate base of acetic acid, has a base dissociation constant (Kb) of
approximately 5.6x10−10 , making it a weak base. In order for a species to have a strong conjugate base it has
to be a very weak acid, like water for example.

Identifying conjugate acid-base pairs

The acid and conjugate base as well as the base and conjugate acid are known as conjugate pairs. When
finding a conjugate acid or base, it is important to look at the reactants of the chemical equation. In this case,
the reactants are the acids and bases, and the acid corresponds to the conjugate base on the product side of the
chemical equation; as does the base to the conjugate acid on the product side of the equation.

To identify the conjugate acid, look for the pair of compounds that are related. The acid–base reaction can be
viewed in a before and after sense. The before is the reactant side of the equation, the after is the product side
of the equation. The conjugate acid in the after side of an equation gains a hydrogen ion, so in the before side
of the equation the compound that has one less hydrogen ion of the conjugate acid is the base. The conjugate
base in the after side of the equation lost a hydrogen ion, so in the before side of the equation, the compound
that has one more hydrogen ion of the conjugate base is the acid.

Consider the following acid–base reaction:

+
HNO3 + H2O → H3O + NO−3

Nitric acid (HNO3 ) is an acid because it donates a proton to the water molecule and its conjugate base is
nitrate (NO−3). The water molecule acts as a base because it receives the Hydrogen Proton and its conjugate
+
acid is the hydronium ion (H3 O ).

Equation Acid Base Conjugate base Conjugate acid

+ +
HClO2 + H2O → ClO−2 + H3O HClO2 H2O ClO−2 H3O
− − − −
ClO + H2O → HClO + OH H2O ClO OH HClO
− −
HCl + H2PO−4 → Cl + H3PO4 HCl H2PO−4 Cl H3PO4

Applications
One use of conjugate acids and bases lies in buffering systems, which include a buffer solution. In a buffer, a
weak acid and its conjugate base (in the form of a salt), or a weak base and its conjugate acid, are used in order
to limit the pH change during a titration process. Buffers have both organic and non-organic chemical
applications. For example, besides buffers being used in lab processes, our blood acts as a buffer to maintain
pH. The most important buffer in our bloodstream is the carbonic acid-bicarbonate buffer, which prevents
drastic pH changes when CO2 is introduced. This functions as such:

Furthermore, here is a table of common buffers.

Buffering agent pKa Useful pH range

Citric acid 3.13, 4.76, 6.40 2.1 - 7.4

Acetic acid 4.8 3.8 - 5.8
KH2PO4, 7.2 6.2 - 8.2

CHES 9.3 8.3–10.3

Borate 9.24 8.25 - 10.25
A second common application with an organic compound would be the production of a buffer with acetic
acid. If acetic acid, a weak acid with the formula CH3 COOH, was made into a buffer solution, it would need
−
to be combined with its conjugate base CH3 COO in the form of a salt. The resulting mixture is called an
acetate buffer, consisting of aqueous CH3 COOH and aqueous CH3 COONa. Acetic acid, along with many
other weak acids, serve as useful components of buffers in different lab settings, each useful within their own
pH range.

An example with an inorganic compound would be the medicinal use of lactic acid’s conjugate base known as
lactate in Lactated Ringer's solution and Hartmann's solution. Lactic acid has the formula C3 H6 O6 and its
conjugate base is used in intravenous fluids that consist of sodium and potassium cations along with lactate and
chloride anions in solution with distilled water. These fluids are commonly isotonic in relation to human blood
and are commonly used for spiking up the fluid level in a system after severe blood loss due to trauma,
surgery, or burn injury.

Table of acids and their conjugate bases

Tabulated below are several examples of acids and their conjugate bases; notice how they differ by just one
proton (H+ ion). Acid strength decreases and conjugate base strength increases down the table.

Acid Conjugate base

+
H2F Fluoronium ion HF Hydrogen fluoride

HCl Hydrochloric acid Cl− Chloride ion

H2SO4 Sulfuric acid −

HSO4 Hydrogen sulfate ion

HNO3 Nitric acid −

NO3 Nitrate ion

H3O+ Hydronium ion H2O Water

− 2−
HSO4 Hydrogen sulfate ion SO4 Sulfate ion

H3PO4 Phosphoric acid −

H2PO4 Dihydrogen phosphate ion

CH3COOH Acetic acid CH3COO− Acetate ion

HF Hydrofluoric acid F− Fluoride ion

H2CO3 Carbonic acid −

HCO3 Hydrogen carbonate ion
H2S Hydrosulfuric acid HS− Hydrogen sulfide ion
− 2−
H2PO4 Dihydrogen phosphate ion HPO4 Hydrogen phosphate ion
+ NH3 Ammonia
NH4 Ammonium ion
H2O Water (pH=7) OH− Hydroxide ion
− 2−
HCO3 Hydrogencarbonate (bicarbonate) ion CO3 Carbonate ion

Table of bases and their conjugate acids

In contrast, here is a table of bases and their conjugate acids. Similarly, base strength decreases and conjugate
acid strength increases down the table.
 Base Conjugate acid

C2H5NH2 Ethylamine C2H5NH+3 Ethylammonium ion

CH3NH2 Methylamine CH3NH+3 Methylammonium ion

NH3 Ammonia NH+4 Ammonium ion

+
C5H5N Pyridine C5H6N Pyridinium

C6H5NH2 Aniline C6H5NH+3 Phenylammonium ion

C6H5CO−2 Benzoate ion C6H6CO2 Benzoic acid

−
F Fluoride ion HF Hydrogen fluoride

3− 2−
PO4 Phosphate ion HPO4 Hydrogen phosphate ion

OH− Hydroxide ion H2O Water (neutral, pH 7)

See also
Buffer solution
Deprotonation
Protonation
Salt (chemistry)

References
1. Zumdahl, Stephen S., & Zumdahl, Susan A. Chemistry. Houghton Mifflin, 2007,
ISBN 0618713700
2. "Brønsted–Lowry theory | chemistry" (https://www.britannica.com/science/Bronsted-Lowry-theor
y). Encyclopedia Britannica. Retrieved 2020-02-25.
3. "Strength of Conjugate Acids and Bases Chemistry Tutorial" (https://www.ausetute.com.au/cab
strength.html). www.ausetute.com.au. Retrieved 2020-02-25.

External links
MCAT General Chemistry Review - 10.4 Titration and Buffers (http://schoolbag.info/chemistry/m
cat_2/78.html)
The Pharmaceutics and Compounding Laboratory - Buffers and Buffer Capacity. (https://pharml
abs.unc.edu/labs/ophthalmics/buffers.htm)

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