Side chain

This article is about the side chain of any type of long molecule. For the substitution of an atom or chemical group for a hydrogen atom on a hydrocarbon chain, see Substituent.

This article is about the chemistry term. For the audio engineering term, see dynamic range compression § Side-chaining. For block chain extension technology, see Block chain (database).

IUPAC definition

Branch
Side-chain
Pendant chain
An oligomeric or polymeric offshoot from a macromolecular chain.

Notes

1. An oligomeric branch may be termed a short-chain branch.
2. A polymeric branch may be termed a long-chain branch.

In organic chemistry and biochemistry, a side chain is a chemical group that is attached to a core part of the molecule called "main chain" or backbone. A side chain is also known as a pendant chain, but a pendant group (side group) has a different definition. The placeholder R is often used as a generic placeholder for alkyl (saturated hydrocarbon) group side chains in chemical structure diagrams. To indicate other non-carbon groups in structure diagrams, X, Y, or Z is often used. The R symbol was introduced by 19th-century French chemist Charles Frédéric Gerhardt, who advocated its adoption on the grounds that it would be widely recognizable and intelligible given its correspondence in multiple European languages to the initial letter of one or more words already used to denote the concept and sharing the meaning "root" or "residue": French racine ("root") and résidu ("residue"), these terms' respective English translations along with radical (itself derived from Latin radix below), Latin radix ("root") and residuum ("residue"), and German Rest ("remnant" and, in the context of chemistry, both "residue" and "radical").

In polymer science, the side chain of an oligomeric or polymeric offshoot extends from the backbone chain of a polymer. Side chains have noteworthy influence on a polymer's properties, mainly its crystallinity and density. An oligomeric branch may be termed a short-chain branch, and a polymeric branch may be termed a long-chain branch. Side groups are different from side chains; they are neither oligomeric nor polymeric.

In proteins, which are composed of amino acid residues, the side chains are attached to the alpha-carbon atoms of the amide backbone. The side chain connected to the alpha-carbon is specific for each amino acid and is responsible for determining charge and polarity of the amino acid. The amino acid side chains are also responsible for many of the interactions that lead to proper protein folding and function.

See also

• Alkyl
• Backbone chain
• Branching (polymer chemistry)
• Functional group
• Pendant group
• Substituent