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A dimer // is a chemical entity consisting of two structurally similar monomers joined by bonds that can be either strong or weak, covalent or intermolecular. The term homodimer is used when the two molecules are identical (e.g. A-A) and heterodimer when they are not (e.g. A-B). The reverse of dimerisation is often called dissociation.
Carboxylic acids form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen when anhydrous. For example, acetic acid forms a dimer in the gas phase, where the monomer units are held together by hydrogen bonds. Under special conditions, most OH-containing molecules form dimers, e.g. the water dimer.
Excimers and exciplexes are excited structures with a short lifetime. For example, noble gases do not form stable dimers, but do form the excimers Ar2*, Kr2* and Xe2* under high pressure and electrical stimulation.
Molecular dimers are often formed by the reaction of two identical compounds e.g.: 2A → A-A. In this example, monomer "A" is said to dimerise to give the dimer "A-A". An example is a diaminocarbene, which dimerise to give a tetraaminoethylene:
- 2 C(NR2)2 → (R2N)2C=C(NR2)2
Carbenes are highly reactive and readily form bonds.
Dicyclopentadiene is an asymmetrical dimer of two cyclopentadiene molecules that have reacted in a Diels-Alder reaction to give the product. Upon heating, it "cracks" (undergoes a retro-Diels-Alder reaction) to give identical monomers:
- C10H12 → 2 C5H6
Many nonmetallic elements occur as dimers: hydrogen, nitrogen, oxygen, the halogens, i.e. fluorine, chlorine, bromine and iodine. Mercury occurs as a mercury(I) cation (Hg22+), formally a heterodimer.
In the context of polymers, "dimer" also refers to the degree of polymerization 2, regardless of the stoichiometry or condensation reactions. This is particularly applicable to disaccharides. For example, cellobiose is a dimer of glucose, even though the formation reaction produces water:
- 2C6H12O6 → C12H22O11 + H2O
Here, the dimer has a stoichiometry different from the pair of monomers.
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- "IUPAC "Gold Book" definition". Retrieved 2009-04-30.