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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
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
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
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
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
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
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
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
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
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
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 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
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
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
Enzyme
rate-limiting proline isomerization process in a protein folding event include: Activation energies consistent with proline isomerization, which typically
Prolyl_isomerase
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
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
Terpene hydrocarbon
limonene isomerizes to the conjugated diene α-terpinene (which can also easily be converted to p-cymene). Evidence for this isomerization includes the
Limonene
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
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 compound
Both isomers are colorless flammable liquids. It is formed by the isomerization of allylbenzene. "Trans-beta-Methylstyrene". Hassam, Mohammad; Taher
Trans-Propenylbenzene
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
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
Process that results in the interconversion of chemical species
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
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
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
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
Brand name for a chemical product
synthesis. Studies have demonstrated catalytic properties in alkylation, isomerization, oligomerization, acylation, ketalization, esterification, hydrolysis
Nafion
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
disulfides, and an isomerization pathway that shuffles incorrectly formed disulfides. The oxidative pathway relies, just like the isomerization pathway, on a
Oxidative_folding
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 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
14-Hydroxy-Colladonin. MHAT-based isomerization operates through a distinct mechanistic route. Co-mediated MHAT has been employed to isomerize terminal alkenes to internal
Metal-hydride hydrogen atom transfer
Metal-hydride_hydrogen_atom_transfer
Basic step in a process
separation, crystallization, evaporation, filtration, polymerization, isomerization, and other reactions. For example, in milk processing, the following
Unit_operation
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
Chemical compound
diterpene family. The compound forms primarily through thermal or chemical isomerization of abietic acid during the distillation and processing of crude rosin
Neoabietic_acid
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)
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
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
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
Chemical equilibrium of a reversible reaction
substance may be written as P(substance). In a simple reaction such as the isomerization: A ↽ − − ⇀ B {\displaystyle {\ce {A <=> B}}} There are two reactions
Dynamic_equilibrium
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
Neutral chemical compound with both a positively- and negatively-charged functional group
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
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
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 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
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
Chemical compound
species of Aster. It is biosynthesized from geranyl pyrophosphate via isomerization to linalyl pyrophosphate. Oxidation of fenchol gives fenchone. Juniperol
Fenchol
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
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)
Chemical reaction involving the formation of sugars from formaldehyde
of 1 with formaldehyde to make glyceraldehyde (2). An aldose-ketose isomerization of 2 forms dihydroxyacetone (3). A further aldol reaction of 3 with
Formose_reaction
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
Type of protein fold
protein fold common to enzymes that catalyze disulfide bond formation and isomerization. The fold is named for the canonical example thioredoxin and is found
Thioredoxin_fold
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
Molecular-scale artificial or biological device
motion in proteins, such as rotation about single bonds or cis-trans isomerization. Different AMMs are produced by introducing various functionalities
Molecular_machine
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
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
Isomer/derivative of butane
industry, such as in the synthesis of isooctane. Isobutane is obtained by isomerization of butane.[citation needed] Isobutane is the principal feedstock in
Isobutane
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
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 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 compound
broken open, making a secosteroid. This then undergoes spontaneous isomerization into cholecalciferol, the prohormone of the active form of vitamin D
Previtamin_D3
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
Chemical compound
It is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. One unusual feature of
Tetrakis(dimethylamino)ethylene
Tetrakis(dimethylamino)ethylene
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
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
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
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
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
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
Joint stock company based in Russia
Design for detailed engineering of isomerization (technology Isomalk-2, isomerization n-butane Isomalk-3, isomerization n-heptane Isomalk-4) and reforming
SIE_Neftehim
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
destroying the carborane cluster, and demonstrated the ortho to meta isomerization. Heteroborane Organoboron chemistry Platonic hydrocarbon Davidson, M
Ortho-Carborane
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
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
base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerization of citrate to isocitrate in the citric acid cycle. It is acted upon
Aconitic_acid
American chemist (1934–2018)
photochemistry. His doctoral dissertation was titled “Photochemical isomerization of eucarvone and cyclooctatrienone; Studies toward the synthesis of
Edward_M._Burgess
Synthesis of THC from CBD
Cain CK, Clark JH (September 1940). "Structure of cannabidiol. VI. Isomerization of cannabidiol to tetrahydrocannabinol, a physiologically active product
Conversion_of_CBD_to_THC
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
Chemical change induced by light
In chemistry, photoisomerization is a form of isomerization induced by photoexcitation. Both reversible and irreversible photoisomerizations are known
Photoisomerization
Number of molecules that participate in a single-step reaction
refers to chemical product(s). The reaction or reaction step is an isomerization if there is only one product molecule, or a dissociation if there is
Molecularity
Chemical process used in oil refining
conversion methylcyclohexane (a naphthene) to toluene (an aromatic): The isomerization of normal paraffins to isoparaffins as exemplified in the conversion
Catalytic_reforming
Chemical compound
241. ISBN 0-12-543562-2. US 4187231, R. L. Cobb, "Cyanide-catalyzed isomerization and deuterium exchange with alpha- and beta-sulfolenes", published 1980-02-05
Sulfolene
Formation of a thioether (–S–) compound from a thiol (–SH) and an alkene ( >C=C< )
the hydrogen addition on the carbon radical determines whether the isomerization product will be cis or trans. Therefore, composition of the products
Thiol-ene_reaction
Cyclic compound (C2H4O)
the C-C bond in acetaldehyde. In absence of a catalyst, the thermal isomerization of ethylene oxide is never selective and apart from acetaldehyde yields
Ethylene_oxide
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
Chemical compound
Dalin (2020). "Synthesis of cis-1,3,3,3-tetrafluoropropene by catalytic isomerization of trans-1,3,3,3-tetrafluoropropene over alumina catalysts". Applied
Cis-1,3,3,3-Tetrafluoropropene
Cis-1,3,3,3-Tetrafluoropropene
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
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
Chemical compound
(CH3CH(OH)CO2H). The enzyme 2-hydroxyisobutyryl coenzyme A (CoA) mutase isomerizes 3-hydroxybutyryl coenzyme A into 2-hydroxyisobutyryl coenzyme A. Hydrolysis
2-Hydroxyisobutyric_acid
Chemical mechanism for isomerization
Chemical mechanism for isomerization
Ray–Dutt_twist
Compound
'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
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
Class of enzymes
oxidoreductase (isomerizing). Other names in common use include dihydroxyisovalerate dehydrogenase (isomerizing), acetohydroxy acid isomeroreductase
Ketol-acid_reductoisomerase
Molecule with ability to reversibly switch states
switches since light can also be used to trigger the isomerization. There mechanism of isomerization is shown in the figure above. Due to their easy synthesis
Molecular_switch
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
Chemical compound
unstable and has not been isolated. Calculations suggest that it would isomerize rapidly into but-2-enedial. Even substituted derivatives, such as 1,4-diphenyl-2
1,2-Dioxin
Class of astringent, bitter plant polyphenolic chemical compounds
Hydrolyzable tannins Phlorotannins Condensed tannins Phlobatannins (C-ring isomerized condensed tannins) Sources Plants Brown algae Plants Tree heartwood
Tannin
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