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<title>Dimerization</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Dimerization</span></span>

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</style><div role="note" class="hatnote navigation-not-searchable">"Dimer (chemistry)" redirects here. For other uses, see <a href="Dimer_(disambiguation)" class="mw-redirect mw-disambig" title="Dimer (disambiguation)">Dimer (disambiguation)</a>.</div>

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<p>In <a href="Chemistry" title="Chemistry">chemistry</a>, <b>dimerization</b> is the process of joining two identical or similar <a href="Molecular_entity" title="Molecular entity">molecular entities</a> by <a href="Chemical_bond" title="Chemical bond">bonds</a>. The resulting bonds can be either strong or weak. Many symmetrical <a href="Chemical_species" title="Chemical species">chemical species</a> are described as <b>dimers</b>, even when the <a href="Monomer" title="Monomer">monomer</a> is unknown or highly unstable.<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

</p><p>The term <i>homodimer</i> is used when the two subunits are identical (e.g. A–A) and <i>heterodimer</i> when they are not (e.g. A–B). The reverse of dimerization is often called <a href="Dissociation_(chemistry)" title="Dissociation (chemistry)">dissociation</a>. When two oppositely-charged <a href="Ion" title="Ion">ions</a> associate into dimers, they are referred to as <i>Bjerrum pairs</i>,<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> after Danish chemist <a href="Niels_Bjerrum" title="Niels Bjerrum">Niels Bjerrum</a>.

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<div class="mw-heading mw-heading2"><h2 id="Noncovalent_dimers">Noncovalent dimers</h2></div>

<p><a href="Anhydrous" title="Anhydrous">Anhydrous</a> <a href="Carboxylic_acid" title="Carboxylic acid">carboxylic acids</a> form dimers by hydrogen bonding of the acidic hydrogen and the carbonyl oxygen. For example, <a href="Acetic_acid" title="Acetic acid">acetic acid</a> forms a dimer in the gas phase, where the monomer units are held together by <a href="Hydrogen_bond" title="Hydrogen bond">hydrogen bonds</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup> Many OH-containing molecules form dimers, e.g. the <a href="Water_dimer" title="Water dimer">water dimer</a>.

</p><p>Dimers that form based on weak <a href="Electrostatic_Interaction" class="mw-redirect" title="Electrostatic Interaction">electrostatic interaction</a> and/or <a href="Van_der_Waals_interactions" class="mw-redirect" title="Van der Waals interactions">van der Waals interactions</a> have a short lifetime, but can be stabilized through special laboratory setups such as <a href="Matrix_isolation" title="Matrix isolation">matrix-isolation</a>. A prominent example is the <a href="Carbon_dioxide" title="Carbon dioxide">carbon dioxide</a> dimer,<sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> which is likely to be relevant to Venus atmosphere. <sup id="cite_ref-5" class="reference"><a href="#cite_note-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>

</p><p><a href="Excimers" class="mw-redirect" title="Excimers">Excimers</a> and <a href="Exciplex" class="mw-redirect" title="Exciplex">exciplexes</a> are <a href="Excited_state" title="Excited state">excited</a> structures with a short lifetime. For example, <a href="Noble_gases" class="mw-redirect" title="Noble gases">noble gases</a> do not form stable dimers, but they do form the <a href="Excimers" class="mw-redirect" title="Excimers">excimers</a> Ar<sub>2</sub>*, Kr<sub>2</sub>* and Xe<sub>2</sub>* under high pressure and electrical stimulation.<sup id="cite_ref-6" class="reference"><a href="#cite_note-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading2"><h2 id="Covalent_dimers">Covalent dimers</h2></div>

<p><a href="Molecular" class="mw-redirect" title="Molecular">Molecular</a> dimers are often formed by the reaction of two identical compounds e.g.: <style data-mw-deduplicate="TemplateStyles:r1123817410">

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</style><span class="chemf nowrap">2A → A−A</span>. In this example, <a href="Monomer" title="Monomer">monomer</a> "A" is said to dimerize to give the dimer "<span class="chemf nowrap">A−A</span>".

</p><p><a href="Dicyclopentadiene" title="Dicyclopentadiene">Dicyclopentadiene</a> is an asymmetrical dimer of two <a href="Cyclopentadiene" title="Cyclopentadiene">cyclopentadiene</a> molecules that have reacted in a <a href="Diels-Alder_reaction" class="mw-redirect" title="Diels-Alder reaction">Diels-Alder reaction</a> to give the product. Upon heating, it "cracks" (undergoes a retro-Diels-Alder reaction) to give identical monomers:

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<annotation encoding="application/x-tex">{\displaystyle {\ce {C10H12 -> 2 C5H6}}}</annotation>

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</math></span><img src="./6992f79c1ec67f8bbc12ec16f4df8f33a00d54ee.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:19.349ex; height:2.843ex;" alt="{\displaystyle {\ce {C10H12 -> 2 C5H6}}}" loading="lazy"></span></dd></dl>

<p>Many nonmetallic elements occur as dimers: <a href="Hydrogen" title="Hydrogen">hydrogen</a>, <a href="Nitrogen" title="Nitrogen">nitrogen</a>, <a href="Oxygen" title="Oxygen">oxygen</a>, and the <a href="Halogen" title="Halogen">halogens</a> <a href="Fluorine" title="Fluorine">fluorine</a>, <a href="Chlorine" title="Chlorine">chlorine</a>, <a href="Bromine" title="Bromine">bromine</a> and <a href="Iodine" title="Iodine">iodine</a>. Some metals form a proportion of dimers in their vapour phase: <a href="Dilithium" title="Dilithium">dilithium</a> (<span class="chemf nowrap">Li<sub class="template-chem2-sub">2</sub></span>), <a href="Disodium" class="mw-redirect" title="Disodium">disodium</a> (<span class="chemf nowrap">Na<sub class="template-chem2-sub">2</sub></span>), <a href="Dipotassium" class="mw-redirect" title="Dipotassium">dipotassium</a> (<span class="chemf nowrap">K<sub class="template-chem2-sub">2</sub></span>), <a href="Dirubidium" title="Dirubidium">dirubidium</a> (<span class="chemf nowrap">Rb<sub class="template-chem2-sub">2</sub></span>) and <a href="Dicaesium" class="mw-redirect" title="Dicaesium">dicaesium</a> (<span class="chemf nowrap">Cs<sub class="template-chem2-sub">2</sub></span>). Such elemental dimers are <a href="Homonuclear_molecule" title="Homonuclear molecule">homonuclear</a> <a href="Diatomic_molecule" title="Diatomic molecule">diatomic molecules</a>.

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<div class="mw-heading mw-heading2"><h2 id="Polymer_chemistry">Polymer chemistry</h2></div>

<p>In the context of <a href="Polymer" title="Polymer">polymers</a>, "dimer" also refers to the <a href="Degree_of_polymerization" title="Degree of polymerization">degree of polymerization</a> 2, regardless of the stoichiometry or <a href="Condensation_reaction" title="Condensation reaction">condensation reactions</a>.

</p><p>One case where this is applicable is with <a href="Disaccharide" title="Disaccharide">disaccharides</a>. For example, <a href="Cellobiose" title="Cellobiose">cellobiose</a> is a dimer of <a href="Glucose" title="Glucose">glucose</a>, even though the formation reaction produces <a href="Water" title="Water">water</a>:

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<annotation encoding="application/x-tex">{\displaystyle {\ce {2 C6H12O6 -> C12H22O11 + H2O}}}</annotation>

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</math></span><img src="./9e0bc0f77f6073d357dd8e19f6e294c75df60df8.svg" class="mwe-math-fallback-image-inline mw-invert skin-invert" aria-hidden="true" style="vertical-align: -1.005ex; width:34.163ex; height:2.843ex;" alt="{\displaystyle {\ce {2 C6H12O6 -> C12H22O11 + H2O}}}" loading="lazy"></span></dd></dl>

<p>Here, the resulting dimer has a stoichiometry different from the initial pair of monomers.

</p><p>Disaccharides need not be composed of the same <a href="Monosaccharide" title="Monosaccharide">monosaccharides</a> to be considered dimers. An example is <a href="Sucrose" title="Sucrose">sucrose</a>, a dimer of <a href="Fructose" title="Fructose">fructose</a> and glucose, which follows the same reaction equation as presented above.

</p><p>Amino acids can also form dimers, which are called <a href="Dipeptide" title="Dipeptide">dipeptides</a>. An example is <a href="Glycylglycine" title="Glycylglycine">glycylglycine</a>, consisting of two <a href="Glycine" title="Glycine">glycine</a> molecules joined by a <a href="Peptide_bond" title="Peptide bond">peptide bond</a>. Other examples include <a href="Aspartame" title="Aspartame">aspartame</a> and <a href="Carnosine" title="Carnosine">carnosine</a>.

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<div class="mw-heading mw-heading2"><h2 id="Inorganic_and_organometallic_dimers">Inorganic and organometallic dimers</h2></div>

<p>Many molecules and ions are described as dimers, even when the monomer is elusive.

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<div class="mw-heading mw-heading3"><h3 id="Boranes">Boranes</h3></div>

<p><a href="Diborane" title="Diborane">Diborane</a> (B<sub>2</sub>H<sub>6</sub>) is an dimer of <a href="Borane" title="Borane">borane</a>, which is elusive and rarely observed. Almost all compounds of the type R2BH exist as dimers.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading3"><h3 id="Organoaluminium_compounds">Organoaluminium compounds</h3></div>

<p><a href="Organoaluminium_chemistry" title="Organoaluminium chemistry">Trialkylaluminium compounds</a> can exist as either monomers or dimers, depending on the <a href="Steric_effects" title="Steric effects">steric bulk</a> of the groups attached. For example, <a href="Trimethylaluminium" title="Trimethylaluminium">trimethylaluminium</a> exists as a dimer, but trimesitylaluminium adopts a monomeric structure.<sup id="cite_ref-:0_8-0" class="reference"><a href="#cite_note-:0-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading3"><h3 id="Organochromium_compounds">Organochromium compounds</h3></div>

<p>Cyclopentadienylchromium tricarbonyl dimer exists in measureable equilibrium quantities with the monometallic radical <span class="chemf nowrap">(C<sub class="template-chem2-sub">5</sub>H<sub class="template-chem2-sub">5</sub>)Cr(CO)<sub class="template-chem2-sub">3</sub></span>.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading2"><h2 id="Biochemical_dimers">Biochemical dimers</h2></div>

<div class="mw-heading mw-heading3"><h3 id="Pyrimidine_dimers">Pyrimidine dimers</h3></div>

<p><a href="Pyrimidine_dimers" class="mw-redirect" title="Pyrimidine dimers">Pyrimidine dimers</a> (also known as thymine dimers) are formed by a <a href="Photochemical_reaction" class="mw-redirect" title="Photochemical reaction">photochemical reaction</a> from pyrimidine <a href="DNA_base" class="mw-redirect" title="DNA base">DNA bases</a> when exposed to ultraviolet light.<sup id="cite_ref-:0_8-1" class="reference"><a href="#cite_note-:0-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> This cross-linking causes <a href="Mutation" title="Mutation">DNA mutations</a>, which can be <a href="Carcinogenic" class="mw-redirect" title="Carcinogenic">carcinogenic</a>, causing <a href="Skin_cancer" title="Skin cancer">skin cancers</a>.<sup id="cite_ref-:0_8-2" class="reference"><a href="#cite_note-:0-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup> When <a href="Pyrimidine_dimer" title="Pyrimidine dimer">pyrimidine dimers</a> are present, they can block <a href="Polymerase" title="Polymerase">polymerases</a>, decreasing DNA functionality until it is repaired.<sup id="cite_ref-:0_8-3" class="reference"><a href="#cite_note-:0-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading3"><h3 id="Protein_dimers">Protein dimers</h3></div>

<p><a href="Protein_dimer" title="Protein dimer">Protein dimers</a> arise from the interaction between two <a href="Protein" title="Protein">proteins</a> which can interact further to form larger and more complex <a href="Oligomer" title="Oligomer">oligomers</a>.<sup id="cite_ref-:1_10-0" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup> For example, <a href="Tubulin" title="Tubulin">tubulin</a> is formed by the dimerization of <a href="Tubulin" title="Tubulin">α-tubulin</a> and <a href="Tubulin" title="Tubulin">β-tubulin</a> and this dimer can then <a href="Polymerization" title="Polymerization">polymerize</a> further to make <a href="Microtubule" title="Microtubule">microtubules</a>.<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> For symmetric proteins, the larger protein complex can be broken down into smaller identical <a href="Protein_subunit" title="Protein subunit">protein subunits</a>, which then dimerize to decrease the genetic code required to make the functional protein.<sup id="cite_ref-:1_10-1" class="reference"><a href="#cite_note-:1-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>

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<div class="mw-heading mw-heading3"><h3 id="G_protein-coupled_receptors">G protein-coupled receptors</h3></div><p>

As the largest and most diverse family of <a href="Receptor_(biochemistry)" title="Receptor (biochemistry)">receptors</a> within the human genome, <a href="G_protein-coupled_receptor" title="G protein-coupled receptor">G protein-coupled receptors</a> (GPCR) have been studied extensively, with recent studies supporting their ability to form dimers.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> GPCR dimers include both homodimers and heterodimers formed from related members of the GPCR family.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> While not all, some GPCRs require dimerization to function, such as <a href="GABAB_receptor" title="GABAB receptor">GABA<sub>B</sub></a>-receptor, emphasizing the importance of dimers in biological systems.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup></p>

<div class="mw-heading mw-heading3"><h3 id="Receptor_tyrosine_kinase">Receptor tyrosine kinase</h3></div>

<p>Much like for G protein-coupled receptors, dimerization is essential for <a href="Receptor_tyrosine_kinase" title="Receptor tyrosine kinase">receptor tyrosine kinases</a> (RTK) to perform their function in <a href="Signal_transduction" title="Signal transduction">signal transduction</a>, affecting many different cellular processes.<sup id="cite_ref-:2_15-0" class="reference"><a href="#cite_note-:2-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> RTKs typically exist as monomers, but undergo a <a href="Conformational_change" title="Conformational change">conformational change</a> upon <a href="Ligand_(biochemistry)" title="Ligand (biochemistry)">ligand</a> binding, allowing them to dimerize with nearby RTKs.<sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The dimerization activates the <a href="Cytoplasm" title="Cytoplasm">cytoplasmic</a> <a href="Kinase" title="Kinase">kinase</a> <a href="Protein_domain" title="Protein domain">domains</a> that are responsible for further <a href="Signal_transduction" title="Signal transduction">signal transduction</a>.<sup id="cite_ref-:2_15-1" class="reference"><a href="#cite_note-:2-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup>

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<div class="side-box-text plainlist">Wikimedia Commons has media related to <a href="https://commons.wikimedia.org/wiki/Dimers" class="extiw external" title="commons:Dimers"><span style="font-style:italic; font-weight:bold;">Dimers</span></a>.</div></div>

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<ul><li><a href="Monomer" title="Monomer">Monomer</a></li>

<li><a href="Trimer_(chemistry)" title="Trimer (chemistry)">Trimer</a></li>

<li><a href="Polymer" title="Polymer">Polymer</a></li>

<li><a href="Protein_dimer" title="Protein dimer">Protein dimer</a></li>

<li><a href="Oligomer" title="Oligomer">Oligomer</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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