Functionality (chemistry)

In chemistry, functionality is the presence of functional groups in a molecule. A monofunctional molecule possesses one functional group, a bifunctional (or difunctional) two, a trifunctional three, and so forth. In organic chemistry (and other fields of chemistry), a molecule's functionality has a decisive influence on its reactivity.

Monofunctional compounds
Methyl acetate
Thiophenol
Ethylamine

Difunctional compounds
Malonic acid
Ethanolamine
Glycine

Trifunctional compounds
Glycerol
(R)-Cysteine

In polymer chemistry, the functionality of a monomer refers to its number of polymerizable groups, and affects the formation and the degree of crosslinking of polymers.

In organic chemistry and material science

In organic chemistry, functionality is often used as a synonym for functional group. For example, a hydroxyl group can also be called a HO-function.^[1][2]

Functionalisation means the introduction of functional groups, for example

• the functionalisation of a surface^[3] (e.g. silanization for the specific modification of the adhesion of a surface)
• the functionalization of nanoparticles of a metal or metal oxide to stabilize such nanoparticles^[4] or
• the so-called C-H functionalization,^[5] which means the substitution of a C-H bond by a functional group, bonded at the same carbon atom

In polymer chemistry

According to IUPAC, the functionality of a monomer is defined as the number of bonds that a monomer's repeating unit forms in a polymer with other monomers. Thus in the case of a functionality of f = 2 a linear polymer is formed by polymerizing (a thermoplastic). Monomers with a functionality f ≥ 3 lead to a branching point, which can lead to cross-linked polymers (a thermosetting polymer). Monofunctional monomers do not exist as such molecules lead to a chain termination.^[6]

From the average functionality of the used monomers the reaching of the gel point can be calculated as a function of reaction progress.^[7] Side reactions may increase or decrease the functionality.^[8]

However, IUPAC definition and the use of the term in organic chemistry differ with respect to the functionality of a double bond.^[6][9] In polymer chemistry, a double bond possesses a functionality of two (because two points of contact for further polymer chains are present, on each of the two adjacent carbon atoms), while in organic chemistry the double bond is a functional group and thus has a functionality of one.