Electron acceptor

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An electron acceptor is a chemical entity that accepts electrons transferred to it from another compound. [1] Electron acceptors are oxidizing agents.

Contents

The electron accepting power of an electron acceptor is measured by its redox potential. [2]

In the simplest case, electron acceptors are reduced by one electron. The process can alter the structure of the acceptor substantially. When the added electron is highly delocalized, the structural consequences of the reduction can be subtle. The central C-C distance in the electron acceptor tetracyanoethylene elongates from 135 to 143 pm upon acceptance of an electron. [3] In the formation of some donor-acceptor complexes, less than one electron is transferred. TTF-TCNQ is an charge transfer complex.

Biology

Paraquat, the dication on the left, functions as an electron acceptor, disrupting respiration in plants. PquatRedox.svg
Paraquat, the dication on the left, functions as an electron acceptor, disrupting respiration in plants.

In biology, a terminal electron acceptor often refers to either the last compound to receive an electron in an electron transport chain, such as oxygen during cellular respiration, or the last cofactor to receive an electron within the electron transfer domain of a reaction center during photosynthesis. All organisms obtain energy by transferring electrons from an electron donor to an electron acceptor.[ citation needed ]

One practical illustration of the role of electron acceptors in biology is the high toxicity of the paraquat. The activity of this broad spectrum herbicide results from the electron acceptor property of N,N'-dimethyl-4,4'-bipyridinium. [4]

Materials science

In some solar cells, the photocurrent entails transfer of electrons from a donor to an electron acceptor. [5]

See also

Related Research Articles

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<span class="mw-page-title-main">Redox</span> Chemical reaction in which oxidation states of atoms are changed

Redox is a type of chemical reaction in which the oxidation states of a reactant change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is the gain of electrons or a decrease in the oxidation state.

<span class="mw-page-title-main">Oxidizing agent</span> Chemical compound used to oxidize another substance in a chemical reaction

An oxidizing agent is a substance in a redox chemical reaction that gains or "accepts"/"receives" an electron from a reducing agent. In other words, an oxidizer is any substance that oxidizes another substance. The oxidation state, which describes the degree of loss of electrons, of the oxidizer decreases while that of the reductant increases; this is expressed by saying that oxidizers "undergo reduction" and "are reduced" while reducers "undergo oxidation" and "are oxidized". Common oxidizing agents are oxygen, hydrogen peroxide, and the halogens.

Viologens are organic compounds with the formula (C5H4NR)2n+. In some viologens, the pyridyl groups are further modified.

<span class="mw-page-title-main">Conductive polymer</span> Organic polymers that conduct electricity

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<span class="mw-page-title-main">Charge-transfer complex</span> Association of molecules in which a fraction of electronic charge is transferred between them

In chemistry, charge-transfer (CT) complex, or electron-donor-acceptor complex, describes a type of supramolecular assembly of two or more molecules or ions. The assembly consists of two molecules that self-attract through electrostatic forces, i.e., one has at least partial negative charge and the partner has partial positive charge, referred to respectively as the electron acceptor and electron donor. In some cases, the degree of charge transfer is "complete", such that the CT complex can be classified as a salt. In other cases, the charge-transfer association is weak, and the interaction can be disrupted easily by polar solvents.

<span class="mw-page-title-main">Flavin adenine dinucleotide</span> Redox-active coenzyme

In biochemistry, flavin adenine dinucleotide (FAD) is a redox-active coenzyme associated with various proteins, which is involved with several enzymatic reactions in metabolism. A flavoprotein is a protein that contains a flavin group, which may be in the form of FAD or flavin mononucleotide (FMN). Many flavoproteins are known: components of the succinate dehydrogenase complex, α-ketoglutarate dehydrogenase, and a component of the pyruvate dehydrogenase complex.

<span class="mw-page-title-main">Radical anion</span> Free radical species

In organic chemistry, a radical anion is a free radical species that carries a negative charge. Radical anions are encountered in organic chemistry as reduced derivatives of polycyclic aromatic compounds, e.g. sodium naphthenide. An example of a non-carbon radical anion is the superoxide anion, formed by transfer of one electron to an oxygen molecule. Radical anions are typically indicated by .

<span class="mw-page-title-main">Organic redox reaction</span> Redox reaction that takes place with organic compounds

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Tetracyanoquinodimethane (TCNQ) is an organic compound with the chemical formula (N≡C−)2C=C6H4=C(−C≡N)2. It is an orange crystalline solid. This cyanocarbon, a relative of para-quinone, is an electron acceptor that is used to prepare charge transfer salts, which are of interest in molecular electronics.

<span class="mw-page-title-main">Radical (chemistry)</span> Atom, molecule, or ion that has an unpaired valence electron; typically highly reactive

In chemistry, a radical, also known as a free radical, is an atom, molecule, or ion that has at least one unpaired valence electron. With some exceptions, these unpaired electrons make radicals highly chemically reactive. Many radicals spontaneously dimerize. Most organic radicals have short lifetimes.

Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications:

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Phosphorus-centered porphyrins are conjugated polycyclic ring systems consisting of either four pyrroles with inward-facing nitrogens and a phosphorus atom at their core or porphyrins with one of the four pyrroles substituted for a phosphole. Unmodified porphyrins are composed of pyrroles and linked by unsaturated hydrocarbon bridges often acting as multidentate ligands centered around a transition metal like Cu II, Zn II, Co II, Fe III. Being highly conjugated molecules with many accessible energy levels, porphyrins are used in biological systems to perform light-energy conversion and modified synthetically to perform similar functions as a photoswitch or catalytic electron carriers. Phosphorus III and V ions are much smaller than the typical metal centers and bestow distinct photochemical properties unto the porphyrin. Similar compounds with other pnictogen cores or different polycyclic rings coordinated to phosphorus result in other changes to the porphyrin’s chemistry.

References

  1. "Electron Acceptor". The IUPAC Compendium of Chemical Terminology . 2014. doi: 10.1351/goldbook.E01976 .
  2. Connelly, N. G.; Geiger, W. E. (1996). "Chemical Redox Agents for Organometallic Chemistry". Chemical Reviews. 96 (2): 877–910. doi:10.1021/cr940053x. PMID   11848774.
  3. Bock, H.; Ruppert, K. (1992). "Structures of charge-perturbed or sterically overcrowded molecules. 16. The cesium tetracyanoethylenide radical salt". Inorganic Chemistry. 31 (24): 5094–5099. doi:10.1021/ic00050a032.
  4. Bockman, T. M.; Kochi, J. K. (1990). "Isolation and Oxidation-Reduction of Methylviologen Cation Radicals. Novel Disproportionation in Charge-Transfer Salts by X-ray Crystallography". The Journal of Organic Chemistry. 55 (13): 4127–4135. doi:10.1021/jo00300a033.
  5. Stoltzfus, Dani M.; Donaghey, Jenny E.; Armin, Ardalan; Shaw, Paul E.; Burn, Paul L.; Meredith, Paul (2016). "Charge Generation Pathways in Organic Solar Cells: Assessing the Contribution from the Electron Acceptor". Chemical Reviews. 116 (21): 12920–12955. doi:10.1021/acs.chemrev.6b00126. PMID   27341081.