Dimerization
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A dimer () ('' di-'', "two" + ''-mer'', "parts") is an
oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...
consisting of two
monomer In chemistry, a monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification Mo ...
s joined by bonds that can be either strong or weak,
covalent A covalent bond is a chemical bond that involves the sharing of electrons to form electron pairs between atoms. These electron pairs are known as shared pairs or bonding pairs. The stable balance of attractive and repulsive forces between atoms ...
or intermolecular. Dimers also have significant implications in polymer chemistry, inorganic chemistry, and biochemistry. 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 dimerization is often called
dissociation Dissociation, in the wide sense of the word, is an act of disuniting or separating a complex object into parts. Dissociation may also refer to: * Dissociation (chemistry), general process in which molecules or ionic compounds (complexes, or salts) ...
. When two oppositely charged ions associate into dimers, they are referred to as ''Bjerrum pairs'', after
Niels Bjerrum Niels Janniksen Bjerrum (11 March 1879 in Copenhagen – 30 September 1958) was a Danish chemist. Niels Bjerrum was the son of ophthalmologist Jannik Petersen Bjerrum, and started to study at University of Copenhagen in 1897. He received his ...
.


Noncovalent dimers

Anhydrous A substance is anhydrous if it contains no water. Many processes in chemistry can be impeded by the presence of water; therefore, it is important that water-free reagents and techniques are used. In practice, however, it is very difficult to achie ...
carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...
s form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen. For example,
acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main component ...
forms a dimer in the gas phase, where the monomer units are held together by
hydrogen bond In chemistry, a hydrogen bond (or H-bond) is a primarily electrostatic force of attraction between a hydrogen (H) atom which is covalently bound to a more electronegative "donor" atom or group (Dn), and another electronegative atom bearing a ...
s. Under special conditions, most OH-containing molecules form dimers, e.g. the
water dimer The water dimer consists of two water (molecule), water molecules loosely bound by a hydrogen bond. It is the smallest water cluster. Because it is the simplest model system for studying hydrogen bonding in water, it has been the target of many ...
.
Excimers An excimer (originally short for excited dimer) is a short-lived dimeric or heterodimeric molecule formed from two species, at least one of which has a valence shell completely filled with electrons (for example, noble gases). In this case, for ...
and exciplexes are excited structures with a short lifetime. For example, noble gases do not form stable dimers, but they do form the
excimers An excimer (originally short for excited dimer) is a short-lived dimeric or heterodimeric molecule formed from two species, at least one of which has a valence shell completely filled with electrons (for example, noble gases). In this case, for ...
Ar2*, Kr2* and Xe2* under high pressure and electrical stimulation.


Covalent dimers

Molecular A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...
dimers are often formed by the reaction of two identical compounds e.g.: . In this example,
monomer In chemistry, a monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification Mo ...
"A" is said to dimerize to give the dimer "". An example is a diaminocarbene, which dimerize to give a
tetraaminoethylene In organic chemistry, tetraaminoethylene is a hypothetical, organic compound with formula or . Like all polyamines that are geminal, this compound has never been synthesised and is believed to be extremely unstable.Stephen A. Lawrence (2004)'' ...
: :2 C(NR2)2 -> (R2N)2C=C(NR2)2
Carbene In organic chemistry, a carbene is a molecule containing a neutral carbon atom with a valence of two and two unshared valence electrons. The general formula is or where the R represents substituents or hydrogen atoms. The term "carbene" ma ...
s are highly reactive and readily form bonds. Dicyclopentadiene is an asymmetrical dimer of two
cyclopentadiene Cyclopentadiene is an organic compound with the chemical formula, formula C5H6.LeRoy H. Scharpen and Victor W. Laurie (1965): "Structure of cyclopentadiene". ''The Journal of Chemical Physics'', volume 43, issue 8, pages 2765-2766. It is often ab ...
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 Hydrogen is the chemical element with the symbol H and atomic number 1. Hydrogen is the lightest element. At standard conditions hydrogen is a gas of diatomic molecules having the formula . It is colorless, odorless, tasteless, non-toxic, an ...
,
nitrogen Nitrogen is the chemical element with the symbol N and atomic number 7. Nitrogen is a nonmetal and the lightest member of group 15 of the periodic table, often called the pnictogens. It is a common element in the universe, estimated at se ...
,
oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements as wel ...
, and the
halogen The halogens () are a group in the periodic table consisting of five or six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts). In the modern IUPAC nomenclature, this group is ...
s (i.e.
fluorine Fluorine is a chemical element with the symbol F and atomic number 9. It is the lightest halogen and exists at standard conditions as a highly toxic, pale yellow diatomic gas. As the most electronegative reactive element, it is extremely reacti ...
,
chlorine Chlorine is a chemical element with the Symbol (chemistry), symbol Cl and atomic number 17. The second-lightest of the halogens, it appears between fluorine and bromine in the periodic table and its properties are mostly intermediate betwee ...
,
bromine Bromine is a chemical element with the symbol Br and atomic number 35. It is the third-lightest element in group 17 of the periodic table (halogens) and is a volatile red-brown liquid at room temperature that evaporates readily to form a simila ...
and iodine). Noble gases can form dimers linked by
van der Waals bond In molecular physics, the van der Waals force is a distance-dependent interaction between atoms or molecules. Unlike ionic or covalent bonds, these attractions do not result from a chemical electronic bond; they are comparatively weak and the ...
s, such as
dihelium The helium dimer is a van der Waals molecule with formula He2 consisting of two helium atoms. This chemical is the largest diatomic molecule—a molecule consisting of two atoms bonded together. The bond that holds this dimer together is so weak ...
or
diargon Diargon or the argon dimer is a molecule containing two argon atoms. Normally, this is only very weakly bound together by van der Waals forces (a van der Waals molecule). However, in an excited state, or ionised state, the two atoms can be more ...
.
Mercury Mercury commonly refers to: * Mercury (planet), the nearest planet to the Sun * Mercury (element), a metallic chemical element with the symbol Hg * Mercury (mythology), a Roman god Mercury or The Mercury may also refer to: Companies * Merc ...
occurs as a mercury(I) cation (), formally a dimeric ion. Other metals may form a proportion of dimers in their vapour phase. Known metallic dimers include
dilithium Dilithium, Li2, is a strongly electrophilic, diatomic molecule comprising two lithium atoms covalently bonded together. Li2 is known in the gas phase. It has a bond order of 1, an internuclear separation of 267.3  pm and a bond energy of 1 ...
(),
disodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable isot ...
(), dipotassium (),
dirubidium Dirubidium is a molecular substance containing two atoms of rubidium found in rubidium vapour. Dirubidium has two active valence electrons. It is studied both in theory and with experiment. The rubidium trimer has also been observed. Synthesis ...
() and dicaesium (). Such elemental dimers are homonuclear diatomic molecules. Many small organic molecules, most notably
formaldehyde Formaldehyde ( , ) (systematic name methanal) is a naturally occurring organic compound with the formula and structure . The pure compound is a pungent, colourless gas that polymerises spontaneously into paraformaldehyde (refer to section F ...
, easily form dimers. The dimer of formaldehyde () is dioxetane (). Borane () occurs as the dimer diborane (), due to the high
Lewis acidity A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...
of the
boron Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the ''boron group'' it has th ...
center.


Polymer chemistry

In the context of
polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
s, "dimer" also refers to the
degree of polymerization The degree of polymerization, or DP, is the number of monomeric units in a macromolecule or polymer or oligomer molecule. For a homopolymer, there is only one type of monomeric unit and the ''number-average'' degree of polymerization is given by ...
2, regardless of the stoichiometry or condensation reactions. One case where this is applicable is with disaccharides. For example,
cellobiose Cellobiose is a disaccharide with the formula (C6H7(OH)4O)2O. It is classified as a reducing sugar. In terms of its chemical structure, it is derived from the condensation of a pair of β-glucose molecules forming a β(1→4) bond. It can be hyd ...
is a dimer of
glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...
, even though the formation reaction produces
water Water (chemical formula ) is an inorganic, transparent, tasteless, odorless, and nearly colorless chemical substance, which is the main constituent of Earth's hydrosphere and the fluids of all known living organisms (in which it acts as a ...
: : 2 C6H12O6 -> C12H22O11 + H2O Here, the resulting dimer has a stoichiometry different from the initial pair of monomers. Disaccharides need not be composed of the same monosaccharides to be considered dimers. An example is
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...
, a dimer of
fructose Fructose, or fruit sugar, is a Ketose, ketonic monosaccharide, simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galacto ...
and glucose, which follows the same reaction equation as presented above. Amino acids can also form dimers, which are called
dipeptide A dipeptide is an organic compound derived from two amino acids. The constituent amino acids can be the same or different. When different, two isomers of the dipeptide are possible, depending on the sequence. Several dipeptides are physiologicall ...
s. An example is glycylglycine, consisting of two glycine molecules joined by a
peptide bond In organic chemistry, a peptide bond is an amide type of covalent chemical bond linking two consecutive alpha-amino acids from C1 (carbon number one) of one alpha-amino acid and N2 (nitrogen number two) of another, along a peptide or protein cha ...
. Other examples include
aspartame Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade names ...
and carnosine.


Inorganic dimers


Group 13 Dimers


Boranes

Diborane (B2H6) is a classic example of an inorganic dimer. Borane does not exist alone as BH3, even though it is often written in that way. B2H6 exists as a structure where two hydrogen atoms bridge the two
boron Boron is a chemical element with the symbol B and atomic number 5. In its crystalline form it is a brittle, dark, lustrous metalloid; in its amorphous form it is a brown powder. As the lightest element of the ''boron group'' it has th ...
atoms. The bridging B-H bonds are lower in
bond order In chemistry, bond order, as introduced by Linus Pauling, is defined as the difference between the number of bonds and anti-bonds. The bond order itself is the number of electron pairs (covalent bonds) between two atoms. For example, in diat ...
than what would be expected for a regular B-H bond (they are lower in bond order than the terminal B-H bonds). This is explained by the bond having three centers but only two electrons, "banana bond", instead of the typical single bond with two centers and two electrons.


Aluminium

Organoaluminium Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer ...
complexes can exist as either monomers or dimers based on the
steric bulk Steric effects arise from the spatial arrangement of atoms. When atoms come close together there is a rise in the energy of the molecule. Steric effects are nonbonding interactions that influence the shape ( conformation) and reactivity of ions ...
of the groups attached. For example,
methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
or ethylaluminium exists as a dimer, but when a bulkier group is added, the complex exists as a monomer, such as trimesitylaluminium.


Biochemical dimers


Pyrimidine Dimers

Pyrimidine dimers (also known as thymine dimers) are formed by a
photochemical reaction Organic photochemistry encompasses organic reactions that are induced by the action of light. The absorption of ultraviolet light by organic molecules often leads to reactions. In the earliest days, sunlight was employed, while in more modern times ...
from pyrimidine
DNA bases Nucleobases, also known as ''nitrogenous bases'' or often simply ''bases'', are nitrogen-containing biological compounds that form nucleosides, which, in turn, are components of nucleotides, with all of these monomers constituting the basic b ...
when exposed to ultraviolet light. This cross-linking causes
DNA mutations In biology, a mutation is an alteration in the nucleic acid sequence of the genome of an organism, virus, or extrachromosomal DNA. Viral genomes contain either DNA or RNA. Mutations result from errors during DNA or viral replication, mitos ...
, which can be
carcinogenic A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive substan ...
, causing skin cancers. When pyrimidine dimers are present, they can block polymerases, decreasing DNA functionality until it is repaired.


Protein Dimers

Protein dimers arise from the interaction between two
proteins Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, respo ...
which can interact further to form larger and more complex oligomers. For example, tubulin is formed by the dimerization of
α-tubulin Tubulin in molecular biology can refer either to the tubulin protein superfamily of globular proteins, or one of the member proteins of that superfamily. α- and β-tubulins polymerize into microtubules, a major component of the eukaryotic cytoske ...
and
β-tubulin Tubulin in molecular biology can refer either to the tubulin protein superfamily of globular proteins, or one of the member proteins of that superfamily. α- and β-tubulins polymerize into microtubules, a major component of the eukaryotic cytoske ...
and this dimer can then polymerize further to make
microtubules Microtubules are polymers of tubulin that form part of the cytoskeleton and provide structure and shape to eukaryotic cells. Microtubules can be as long as 50 micrometres, as wide as 23 to 27  nm and have an inner diameter between 11 an ...
. For symmetric proteins, the larger protein complex can be broken down into smaller identical protein subunits, which then dimerize to decrease the genetic code required to make the functional protein.


G protein-coupled Receptors

As the largest and most diverse family of receptors within the human genome, G protein-coupled receptors (GPCR) have been studied extensively, with recent studies supporting their ability to form dimers. GPCR dimers include both homodimers and heterodimers formed from related members of the GPCR family. While not all, some GPCRs require dimerization to function, such as GABAB-receptor, emphasizing the importance of dimers in biological systems.


Receptor Tyrosine Kinase

Much like for G protein-coupled receptors, dimerization is essential for receptor tyrosine kinases (RTK) to perform their function in
signal transduction Signal transduction is the process by which a chemical or physical signal is transmitted through a cell as a series of molecular events, most commonly protein phosphorylation catalyzed by protein kinases, which ultimately results in a cellula ...
, affecting many different cellular processes. RTKs typically exist as monomers, but undergo a
conformational change In biochemistry, a conformational change is a change in the shape of a macromolecule, often induced by environmental factors. A macromolecule is usually flexible and dynamic. Its shape can change in response to changes in its environment or oth ...
upon
ligand In coordination chemistry, a ligand is an ion or molecule (functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's electr ...
binding, allowing them to dimerize with nearby RTKs. The dimerization activates the
cytoplasmic In cell biology, the cytoplasm is all of the material within a eukaryotic cell, enclosed by the cell membrane, except for the cell nucleus. The material inside the nucleus and contained within the nuclear membrane is termed the nucleoplasm. Th ...
kinase In biochemistry, a kinase () is an enzyme that catalyzes the transfer of phosphate groups from high-energy, phosphate-donating molecules to specific substrates. This process is known as phosphorylation, where the high-energy ATP molecule don ...
domains that are responsible for further
signal transduction Signal transduction is the process by which a chemical or physical signal is transmitted through a cell as a series of molecular events, most commonly protein phosphorylation catalyzed by protein kinases, which ultimately results in a cellula ...
.


See also

*
Monomer In chemistry, a monomer ( ; ''mono-'', "one" + '' -mer'', "part") is a molecule that can react together with other monomer molecules to form a larger polymer chain or three-dimensional network in a process called polymerization. Classification Mo ...
* Trimer *
Polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...
*
Protein dimer In biochemistry, a protein dimer is a macromolecular complex formed by two protein monomers, or single proteins, which are usually non-covalently bound. Many macromolecules, such as proteins or nucleic acids, form dimers. The word ''dimer'' ha ...
*
Oligomer In chemistry and biochemistry, an oligomer () is a molecule that consists of a few repeating units which could be derived, actually or conceptually, from smaller molecules, monomers.Quote: ''Oligomer molecule: A molecule of intermediate relativ ...


References

* {{cite journal , url=http://goldbook.iupac.org/D01744.html , title=IUPAC "Gold Book" definition , doi=10.1351/goldbook.D01744 , s2cid=242984652 , access-date=2009-04-30 Chemical compounds