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Transformation of the chemical structure of a molecule or ion
structure. Enolization is an example of isomerization, as is tautomerization. When the activation energy for the isomerization reaction is sufficiently small,
Isomerization
Chemical compounds with the same molecular formula but different atomic arrangements
isomerism Cyclohexane conformation Descriptor (chemistry) Electromerism Isomerization Isomery (botany) Ligand isomerism Nuclear isomer Stereocenter Structural
Isomer
Pairs of molecules with same chemical formula showing different spatial orientations
Cis–trans isomerism, also known as geometric isomerism, describes certain arrangements of atoms within molecules. The prefixes "cis" and "trans" are from
Cis–trans_isomerism
Two phenyl rings linked by a N=N double bond
forward and reverse isomerization. Under illumination, these molecules cycle between the two isomeric states. The photo-isomerization of azobenzene is extremely
Azobenzene
disulfides, and an isomerization pathway that shuffles incorrectly formed disulfides. The oxidative pathway relies, just like the isomerization pathway, on a
Oxidative_folding
Molecule interconvertable with another through pericyclic reactions
lab. Some have been observed to isomerize to benzene, whereas others tend to undergo other reactions instead, or isomerize by ways other than pericyclic
Valence_isomer
Covalent bond between amino acids in a protein chain
cis-trans isomerization of X-Pro peptide bonds. Conformational protein folding is usually much faster (typically 10–100 ms) than cis-trans isomerization (10–100 s)
Peptide_bond
Dicarboxylic acid
maleic acid is its conversion to fumaric acid. This conversion, an isomerization, is catalysed by a variety of reagents, such as mineral acids and thiourea
Maleic_acid
In epigenetics, proline isomerization is the effect that cis-trans isomerization of the amino acid proline has on the regulation of gene expression. Similar
Proline isomerization in epigenetics
Proline_isomerization_in_epigenetics
seconds or minutes under ambient conditions. Thermal isomerization is also possible. In E-Z isomerization, the thermal equilibrium lies well towards the trans-form
Diarylethene
Chemical compound
limonene isomerizes to the conjugated diene α-terpinene (which can also easily be converted to p-cymene). Evidence for this isomerization includes the
Limonene
Synthetic materials with properties similar to natural resins
fumarate form is known to react more rapidly with the styrene radical, so isomerization catalysts, such as N,N-dimethylacetoacetamide (DMAA), are often employed
Synthetic_resin
Chemical compound
aromatic–proline peptide bonds. From a kinetic standpoint, cis–trans proline isomerization is a very slow process that can impede the progress of protein folding
Proline
Chemical group (>C=N(O)–)
In organic chemistry, a nitrone is a functional group consisting of an N-oxide of an imine. The general structure is R1R2C=N+(−O−)(−R3), where R3 is not
Nitrone
Epoxide isomerization process
Base-promoted epoxide isomerization is the conversion of alkyl epoxides to ring-opened products through the action of strong base. Isomerizations of this type
Base-promoted epoxide isomerization
Base-promoted_epoxide_isomerization
Type of enzymes
irreversible. Isomerization involves transforming a molecule so that it adopts a different structural conformation; proline isomerization plays an integral
Histone-modifying_enzymes
Reversible chemical transformation by absorption of electromagnetic radiation
some extent. Photochromic systems rely on irradiation to induce the isomerization. Some rely on irradiation for the reverse reaction, others use thermal
Photochromism
Rearrangement reaction
In carbohydrate chemistry, the Lobry de Bruyn–Van Ekenstein transformation also known as the Lobry de Bruyn–Alberda van Ekenstein transformation is the
Lobry de Bruyn–Van Ekenstein transformation
Lobry_de_Bruyn–Van_Ekenstein_transformation
haloalkenes to haloalkanes. MHAT-based isomerization complements the many coordinative methods for alkene isomerization but benefits from its outer-sphere
Metal-hydride hydrogen atom transfer
Metal-hydride_hydrogen_atom_transfer
Chemical compound
volatile colorless liquid, it is highly strained molecule (78.7 kcal/mol). Isomerization of quadricyclane proceeds slowly at low temperatures. Because of quadricyclane's
Quadricyclane
Zeolite used as a catalyst in oil refining
reactions such as hydrocarbon isomerization and the alkylation of hydrocarbons. One such reaction is the isomerization of meta-xylene to para-xylene.
ZSM-5
Class of enzymes
hydratase; EC 4.2.1.3) is an enzyme that catalyses the stereo-specific isomerization of citrate to isocitrate via cis-aconitate in the tricarboxylic acid
Aconitase
Chemical compound
QCISD(T). The large energy barriers between these structures do not make isomerization possible. HOBrO2 is the most stable isomer and is the one pictured above
Bromic_acid
Facility that processes crude oil
blended into the finished gasoline pool immediately or hydrogenated. Isomerization converts linear molecules such as normal pentane to higher-octane branched
Oil_refinery
2005 deadly refinery accident
2005, a hydrocarbon vapor cloud ignited and violently exploded at the isomerization process unit of the BP-owned oil refinery in Texas City, Texas. The
Texas_City_refinery_explosion
Compound with a metal center bound to ligands
A coordination complex is a chemical compound consisting of a central atom or ion, which is usually metallic and is called the coordination centre, and
Coordination_complex
Type of saturated hydrocarbon compound
Dragan and his colleague were the first to report about isomerization in alkanes. Isomerization and reformation are processes in which straight-chain alkanes
Alkane
Chemical equilibrium of a reversible reaction
substance may be written as P(substance). In a simple reaction such as the isomerization: A↽−−⇀B There are two reactions to consider, the forward reaction in
Dynamic_equilibrium
Chemical compound
Arnott, Gareth E.; Green, Ivan R.; van Otterlo, Willem A. L. (2015). "Isomerization of Allylbenzenes". Chemical Reviews. 115 (11): 5462–5569. doi:10.1021/acs
Allylbenzene
Chemical compound
naphthalene with sodium in ethanol. 1,4-Dihydronaphthalene is unstable and can isomerize to 1,2-dihydronaphthalene in a solution of sodium ethoxide in ethanol:
1,4-Dihydronaphthalene
Brand name for a chemical product
synthesis. Studies have demonstrated catalytic properties in alkylation, isomerization, oligomerization, acylation, ketalization, esterification, hydrolysis
Nafion
Continuous catalytic process used in the refining of cruel oil
Platinum Metals Rev. 3 (1) (9). "18,000 BPD C5/C6 Isomerization for Sale at Phoenix Equipment | Isomerization Units for Sale". www.phxequip.com. Retrieved
Penex
Chemical compound
Both isomers are colorless flammable liquids. It is formed by the isomerization of allylbenzene. "Trans-beta-Methylstyrene". Hassam, Mohammad; Taher
Trans-Propenylbenzene
Basic step in a process
separation, crystallization, evaporation, filtration, polymerization, isomerization, and other reactions. For example, in milk processing, the following
Unit_operation
Mammalian protein found in Homo sapiens
for isomerization. At this point, Glu357 deprotonates C2 to create a cis-enediolate intermediate stabilized by Arg272. To complete the isomerization, Glu357
Glucose-6-phosphate_isomerase
Mechanism for unimolecular reactions
model gas phase decomposition or isomerization reactions. Although the net formula for decomposition or isomerization appears to be unimolecular and suggests
Lindemann_mechanism
Enzyme
rate-limiting proline isomerization process in a protein folding event include: Activation energies consistent with proline isomerization, which typically
Prolyl_isomerase
Oil refinery in Texas, US
000 Naphtha Reformer Feed Hydrotreating 166,300 Heavy Gas Oil Hydrotreating 23,300 Isomerization (C5/C6) 38,600 Isomerization (C4) 14,600 Lubes 9,000
ExxonMobil_Beaumont_Refinery
Class of enzymes which convert a molecule between isomeric forms
isomers. The prevalence of each isomer in nature depends in part on the isomerization energy, the difference in energy between isomers. Isomers close in energy
Isomerase
Chemical reaction
chains. Zipper isomerization was first reported by Alexey Favorsky in 1887. The alkyne zipper occurs through repeated isomerizations between an alkyne
Alkyne_zipper_reaction
Chemical change induced by light
In chemistry, photoisomerization is a form of isomerization induced by photoexcitation. Both reversible and irreversible photoisomerizations are known
Photoisomerization
Hydrocarbon compound containing one or more C≡C bonds
constant of alkyne/allene isomerization is generally within several orders of magnitude of unity. For example propyne can be isomerized to give an equilibrium
Alkyne
Unimolecular reactions
showed that the isomerization of azulene to naphthalene is not readily reversible ( the free energy of a naphthalene to azulene isomerization was too high
Thermal rearrangement of aromatic hydrocarbons
Thermal_rearrangement_of_aromatic_hydrocarbons
Chemical reaction
because the milder conditions minimize side reactions, such as alkene isomerization. In the development of Cram's rule, structural assignment of the reaction
Chugaev_elimination
Aromatic, boron-containing rings
Borepins are a class of boron-containing heterocycles used in main group chemistry. They consist of a seven-membered unsaturated ring with a tricoordinate
Borepin
Chemical compound
complex containing a carbocation that can be used as a catalyst for isomerization and disproportionation of alkanes. Isopropyl fluoride can be synthesized
Isopropyl_fluoride
RNA family
involve the addition of water. Rather, the cleavage reaction is simply an isomerization that consists of rearrangement of the linking phosphodiester bond. It
Hammerhead_ribozyme
Molecule containing an equal number of positive and negative functional groups
an uncharged "parent" molecule. Betaines are zwitterions that cannot isomerize to an all-neutral form, such as when the positive charge is located on
Zwitterion
Chemical compound
is useful in conducting experiments with flash photolysis due to the isomerization effect between the trans-4A4N and cis-4A4N states that occurs during
Disperse_Orange_1
Flower used to flavour beer and other beverages
acids or humulones. During wort boiling, the humulones are thermally isomerized into iso-alpha acids or isohumulones, which give a bitter flavour to beer
Hops
Chemical compound
species of Aster. It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate. Oxidation of fenchol gives fenchone. Juniperol
Fenchol
Group of chemical compounds
in beer from the addition of hops to the boiling wort. The degree of isomerization and the amount of bitter flavor produced by the addition of hops is
Alpha_acid
Isomer/derivative of butane
forming the constitutional isomer n-butane. Isobutane is obtained by isomerization of butane.[citation needed] Isobutane is the principal feedstock in
Isobutane
Type of pseudorotation in chemistry
mechanism, is a type of vibration causing molecules of certain geometries to isomerize by exchanging the two axial ligands (see the figure) for two of the equatorial
Berry_mechanism
Methods of measurement of beer
used during brewing. During the brewing process, humulone undergoes isomerization to form both cis- and trans- isohumulone which are responsible for the
Beer_measurement
Chemical compound
Poland from the 1950s to the 1990s under trade name Ipronal. Valofane isomerizes to proxibarbal in vivo. Zajdel P, Kulig K, Zejc A (2008). Zejc A, Gorczyca
Proxibarbital
Chemical compound
cyanide ligands prefer to coordinate at carbon, with a 0.3‑kcal/mol isomerization barrier. When this salt is heated to 500 °C, it decomposes to magnesium
Magnesium_cyanide
Class of chemical compounds
1-alkenes (CH2=CH-(CH2)n-CH3, produced by oligomerization of ethylene) are isomerized on magnesium oxide catalysts with displacement of the double bond to a
Alkenylsuccinic_anhydrides
Class of enzymes
more-reactive electrophile dimethylallyl pyrophosphate (DMAPP). This isomerization is a key step in the biosynthesis of isoprenoids through the mevalonate
Isopentenyl-diphosphate delta isomerase
Isopentenyl-diphosphate_delta_isomerase
Coenzyme
'conventional' photo receptors as the signaling state and not an E/Z isomerization. FMN is called a mononucleotide because it consists of the nitrogenous
Flavin_mononucleotide
Neutral chemical compounds
adjacent to the cationic site. They are thus zwitterions, but cannot isomerize because there is no labile hydrogen atom attached to the nitrogen atom
Betaine
Chemical reagent
each contains a glucose with a free reducing aldehyde moiety after isomerization. Sucrose (table sugar) contains two sugars (fructose and glucose) joined
Benedict's_reagent
InterPro Family
DXP reductoisomerase (1-deoxy-D-xylulose 5-phosphate reductoisomerase or DXR) is an enzyme that interconverts 1-deoxy-D-xylulose 5-phosphate (DXP) and
DXP_reductoisomerase
Member of the Asp/Glu racemase superfamily
discovered in bacteria. It is responsible for catalyzing cis-trans isomerization of the C2-C3 double bond in maleate to produce fumarate, which is a
Maleate_isomerase
Chemical compound
catalyst loading. Besides hydrogenation, the catalyst catalyzes the isomerization and hydroboration of alkenes. Crabtree's catalyst is used in isotope
Crabtree's_catalyst
cis-trans isomerase is an enzyme that catalyzes the conversion, or isomerization, of a small molecule or moiety between its cis and trans geometric isomers
Cis-trans_isomerase
Sub-discipline of chemistry
include cis-trans isomerization and cycloaddition to other (ground state) alkene to give cyclobutane derivatives. The cis-trans isomerization of a (poly)alkene
Photochemistry
Organic chemical transformation
rearrangement is an organic chemical transformation that involves the isomerization of a 1,2-divinylcyclopropane into a cycloheptadiene or -triene. It is
Divinylcyclopropane-cycloheptadiene rearrangement
Divinylcyclopropane-cycloheptadiene_rearrangement
Chemical process used in oil refining
conversion methylcyclohexane (a naphthene) to toluene (an aromatic): The isomerization of normal (meaning straight chain) paraffins to isoparaffins as exemplified
Catalytic_reforming
Process that leads to chemical changes
molecule is involved in a unimolecular reaction; it is transformed by isomerization or a dissociation into one or more other molecules. Such reactions require
Chemical_reaction
Oil refining facility in the Port of New York and New Jersey, United States
Hydrotreating 65,500 Diesel Hydrotreating 108,000 Other Distillate Hydrotreating 17,500 Alkylation 18,800 Isobutane Isomerization 4,000 Hydrogen mmscf/d 22
Bayway_Refinery
Chemical compound
cytochrome-P450. It is significant because it causes DNA alkylation. It isomerizes to chloroacetaldehyde, which modifies adenosine residues by conversion
Chloroethylene_oxide
Field of study
catalyst such as in olefin hydroformylation, olefin hydrogenation, olefin isomerization and the Monsanto process. Organometallic rhodium compounds share many
Organorhodium_chemistry
Chemical compound
neroli, ginger oil, valerian, and mango. It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as
Camphene
Chemical compound
5-phosphate can reversibly isomerize to ribose 5-phosphate. Ribulose 5-phosphate can alternatively undergo a series of isomerizations as well as transaldolations
Ribose_5-phosphate
Chemical reaction used in organic synthesis
rapid equilibrium with its trans-isomer. There are multiple reasons why isomerization is favored here. First, a bulky ligand set is usually used in these
Stille_reaction
Protein-coding gene in the species Homo sapiens
nucleus Biological process rRNA processing protein peptidyl-prolyl isomerization Sources:Amigo / QuickGO Orthologs Databases NCBI: entry; OMA: entry
Peptidyl-prolyl cis-trans isomerase NIMA-interacting 4
Peptidyl-prolyl_cis-trans_isomerase_NIMA-interacting_4
Cross-coupling reaction between boronic acid & an organohalide
of that double bond, cis or trans is determined by the cis-to-trans isomerization of the palladium complex in the oxidative addition step where the trans
Suzuki_reaction
Chemical reaction
organic reaction describing (in its original scope) the dimerization or isomerization of electron-deficient alkenes such as enones by action of an organophosphine
Rauhut–Currier_reaction
Chemical reaction
The Payne rearrangement is the isomerization, under basic conditions, of 2,3-epoxy alcohols to isomeric 1,2-epoxy alcohols with inversion of configuration
Payne_rearrangement
Vision proteins
protein absorbs a photon, the retinal isomerizes and is released by the opsin. The process that follows the isomerization and renewal of retinal is known as
Vertebrate_visual_opsin
Chemical compound
a classic example of a photochemical reaction involving trans-cis isomerization, and can undergo further reaction to form phenanthrene. (E)-Stilbene
(E)-Stilbene
Dutch chemist (1944–2024)
Nolte, Synthese en isomerisatie van polyisocyaniden (Synthesis and isomerization of polyisocyanides), thesis Utrecht 1973". In Memoriam Prof. Roeland
Roeland_Nolte
Class of enzymes
oxidoreductase (isomerizing). Other names in common use include dihydroxyisovalerate dehydrogenase (isomerizing), acetohydroxy acid isomeroreductase
Ketol-acid_reductoisomerase
Former oil refinery in Wales, United Kingdom
Catalytic cracking 37,000 Naphtha hydrotreating 18,300 Catalytic reforming 18,300 Distillate hydrotreating 74,000 Isomerization 11,300 Alkylation 6,300
Milford_Haven_Refinery
American chemist (1934–2018)
photochemistry. His doctoral dissertation was titled “Photochemical isomerization of eucarvone and cyclooctatrienone; Studies toward the synthesis of
Edward_M._Burgess
Jet fuel
is produced by catalytic hydrogenation of dicyclopentadiene and then isomerization. It superseded JP-9, which is a mixture of norbornadiene-based RJ-5
JP-10_(fuel)
Class of organic compounds used as dye
Trans-cis isomerization of azo-POSS, leading to the folding the dodecyl alkyl tail on the POSS head
Azo_dye
Pharmaceutical compound
(1991). "Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment illustrating amine-catalyzed alkene isomerization, stereochemical
Dimethyl_fumarate
Organic reaction
bond activations are alkene isomerization. At least two mechanisms are recognized. For alkene-metal hydrides, isomerization can proceed via migratory insertion
Carbon–hydrogen bond activation
Carbon–hydrogen_bond_activation
Chemical compound
temperature. In the laboratory, citraconic acid can be produced by thermal isomerization of itaconic acid anhydride to give citraconic anhydride, which can be
Citraconic_acid
Superacid system prepared from a Brønsted and a Lewis superacid
liquid media. Magic acid and other superacids are also used to catalyze isomerization of saturated hydrocarbons, and have been shown to protonate even weak
Magic_acid
fact may cause isomerization of 5 into 6 at elevated temperature. Indeed, the calculated activation barriers for the 5 → 6 isomerization via the retro-Diels–Alder
Thermodynamic and kinetic reaction control
Thermodynamic_and_kinetic_reaction_control
Type of molecule
supports cis-/trans- isomerization of polyenes favoring the hula twist rather than the one-bond-flip. The one-bond-flip isomerizes at the reactive double
Photoswitch
Chemical compound
Heard, George L.; Setser, D. W.; Holmes, Bert E. (30 September 2010). "Isomerization of Neopentyl Chloride and Neopentyl Bromide by a 1,2-Interchange of
1-Bromo-2,2-dimethylpropane
Type of unsaturated fat
margarine, one of the original uses for fat hydrogenation. However, an isomerization side reaction during fat hydrogenation can convert remaining unsaturated
Trans_fat
Chemical compound
Grant, R. C. S.; Swinbourne, E. S. (1 January 1966). "The thermal isomerization of chlorocyclopropane and of bromocyclopropane". Chemical Communications
Bromocyclopropane
Badet-Denisot MA, Badet B (1999). "The mechanism of sugar phosphate isomerization by glucosamine 6-phosphate synthase". Protein Sci. 8 (3): 596–602. doi:10
Glutamine—fructose-6-phosphate transaminase (isomerizing)
Glutamine—fructose-6-phosphate_transaminase_(isomerizing)
Metabolic pathway
Methylcitrate dehydratase, methylaconitate cis-trans isomerase and aconitase Isomerization 2-methylcitrate is dehydrated to methylaconitate either by methylcitrate
Methylcitrate_cycle
systematic name of this enzyme class is tetrahydroxypteridine lyase (isomerizing). It employs one cofactor, NAD+. Mcnutt WS, Damle SP (December 1964)
Tetrahydroxypteridine cycloisomerase
Tetrahydroxypteridine_cycloisomerase
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