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Isomers of chemical compounds that interconvert
In chemistry, tautomers (/ˈtɔːtəmər/) are a subset of structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The
Tautomer
Organic compound with a C=C–OH group
Keto-enol tautomerism examples In organic chemistry, enols are a type of functional group or intermediate in organic chemistry. Formally, enols are derivatives
Enol
Organic chemical compound CH3–C(=O)–CH2–C(=O)–CH3
It exists in equilibrium with a tautomer CH3−C(=O)−CH=C(−OH)−CH3. The mixture is a colorless liquid. These tautomers interconvert so rapidly under most
Acetylacetone
Chemical compound belonging to the class of triazine
interconvert between several structures via lactam–lactim tautomerism. Although the triol tautomer may have aromatic character, the keto form predominates
Cyanuric_acid
Chemical compound
nominal formula (H2N)(HN)CN(CH3)CH2CO2H and in solutions, exists in various tautomers, including a neutral form and zwitterionic forms. Creatine was first identified
Creatine
Heterocyclic aromatic organic compound
class of molecules, purines, which include substituted purines and their tautomers. They are the most widely occurring nitrogen-containing heterocycles in
Purine
Physical phenomenon
different minimum-energy tautomers in different electronic states, and if the molecular structure of minimum-energy tautomer in the excited state is proton-transferred
Excited state intramolecular proton transfer
Excited_state_intramolecular_proton_transfer
Organic compound (C6H5OH)
classified as a hard acid. Phenol exhibits keto-enol tautomerism with its unstable keto tautomer cyclohexadienone, but the effect is nearly negligible
Phenol
Chemical compound
that its tautomer is a subunit in some commercial dyes. In solution, 1,3-cyclobutanedione exists in equilibrium with a less stable tautomer, called squaraine
1,3-Cyclobutanedione
Chemical compound
It functions as a reducing agent. It is a white solid, and exhibits tautomerism in solution. Crystalline and gaseous thiourea dioxide adopts a C2v-symmetric
Thiourea_dioxide
Chemical compound
equilibrium with the minor tautomer HP(OH)2. Sometimes the minor tautomer is called hypophosphorous acid and the major tautomer is called phosphinic acid
Hypophosphorous_acid
Chemical compound (H3PO3)
exists in equilibrium with an extremely minor tautomer P(OH)3. (In contrast, arsenous acid's major tautomer is the trihydroxy form.) IUPAC recommends that
Phosphorous_acid
Chemical compound or ion
solution as a mixture of two tautomers. One tautomer has the proton attached to one of the three oxygen atoms. In the second tautomer the proton resides on sulfur
Bisulfite
Molecule containing an equal number of positive and negative functional groups
a phosphonium group and a carboxylate group cannot isomerize. Because tautomers are different compounds, they have distinct structures. By detecting each
Zwitterion
Chemical compound (H–C≡N–O)
H−C≡N+−O−. It is an isomer of isocyanic acid (H−N=C=O) and of its elusive tautomer, cyanic acid (H−O−C≡N), and also of isofulminic acid (H−O−N+≡C−). Fulminate
Fulminic_acid
Phenomenon in materials science
Three tautomers of ranitidine: enamine, imine, and nitronic acid. Each can exist as E/Z isomers.
Disappearing_polymorph
Organic compounds with the structure R–S(=O)2–OH
substituent replaced by hydrogen) is the parent sulfonic acid, HS(=O)2(OH), a tautomer of sulfurous acid, S(=O)(OH)2. Salts or esters of sulfonic acids are called
Sulfonic_acid
Chemical compound
toward hydroxide. Because the triaminobenzene also exists as its imine tautomer, it is susceptible to hydrolysis. Phloroglucinol is a weak triprotic acid
Phloroglucinol
Chemical compound
acetate is an organic compound, which is the acetate ester of the enol tautomer of acetone. This colorless liquid is significant commercially as the principal
Isopropenyl_acetate
Chemical compound
1,4-Diazepine Names IUPAC names Tautomer with N-H bond: 1H-1,4-diazepine (the structure shown above) Tautomer without N-H bond: 2H-1,4-diazepine Identifiers
1,4-Diazepine
Chemical compound
exists a keto-enol tautomerism with its enol tautomer 4-hydroxypyridine. In solution, the keto tautomer is favoured, and the enol tautomer only becomes important
4-Pyridone
Chemical compound
known as dimethyl hydrogen phosphite (DMHP). Dimethylphosphite, is a minor tautomer of the phosphorus(V) derivative. It is a reagent for generating other organophosphorus
Dimethyl_phosphite
Chemical compound, tautomer of hydrogen cyanide
isocyanide is a chemical with the molecular formula HNC. It is a minor tautomer of hydrogen cyanide (HCN). Its importance in the field of astrochemistry
Hydrogen_isocyanide
Chemical compound (H–S–C≡N)
structure H−S−C≡N, which exists as a tautomer with isothiocyanic acid (H−N=C=S). The isothiocyanic acid tautomer tends to dominate with the compound being
Thiocyanic_acid
Chemical compound
Also classified as a heterocyclic compound it is a bicyclic urea. It is a tautomer of 2-hydroxybenzimidazole. The parent compound is prepared by the carbonylation
Benzimidazolinone
Chemical compound
explicable with reference to its tautomerism, which produces a small amount of the keto tautomer. One consequence of this tautomerism is the Bucherer reaction:
1-Naphthol
Chemical compound
formula H2POH. It exists, fleetingly, as a mixture with its less stable tautomer H3PO (phosphine oxide). This mixture has been generated by low temperature
Phosphinous_acid
Chemical compound
malonate via a Michael addition reaction. Dimedone is in equilibrium with its tautomer in solution — in a 2:1 keto to enol ratio in chloroform. Crystalline dimedone
Dimedone
Chemical compound
case of a compound that exists as tautomers. The second tautomer is 2-hydroxypyridine. This lactam lactim tautomerism can also be exhibited in many related
2-Pyridone
Chemical compounds with the same molecular formula but different atomic arrangements
order. For the same reason, there is only one cyclopropene, not three. Tautomers are structural isomers which readily interconvert, so that two or more
Isomer
Chemical compound
for cyclohexanedione hydrolase. The compound exists mainly as the enol tautomer. 1,3-Cyclohexanedione is produced by semi-hydrogenation of resorcinol:
1,3-Cyclohexanedione
Organic compound containing the functional group R–CH=O
or the enol tautomer. Keto–enol tautomerism is catalyzed by either acid or base. In neutral solution, the enol is the minority tautomer, reversing several
Aldehyde
Chemical compound
are known as the N3-H or N1-H tautomers. In the N1-H tautomer, the NH group is nearer the backbone. These neutral tautomers, also referred to as Nε (or
Histidine
Organic compound involved in immune responses
denoted by the pi sign. The tele tautomer, Nτ-H-histamine, is preferred in solution as compared to the pros tautomer, Nπ-H-histamine. Histamine has two
Histamine
Type of organic chemical compound
with ketenes, much like enols can with aldehydes and ketones. The ynol tautomer is usually unstable, does not survive long, and changes into the ketene
Alkynol
Chemical compound
is an organic compound related to 1,2-cyclopentanedione. It is the enol tautomer of the diketone 3-methylcyclopentane-1,2-dione. Being an enol, the compound
2-Hydroxy-3-methyl-2-cyclopenten-1-one
2-Hydroxy-3-methyl-2-cyclopenten-1-one
exist in equilibrium with their enol tautomer, nitro compounds exist in equilibrium with their nitronate tautomer under basic conditions. In practice they
Nitronate
Chemical compound
synthesis of L-cysteine, an amino acid. ACTA exists in equilibrium with its tautomer 2-iminothiazolidine-4-carboxylic acid. It is produced by the reaction of
2-Aminothiazoline-4-carboxylic acid
2-Aminothiazoline-4-carboxylic_acid
Identifier for chemical substances
charge information. Not all layers have to be provided; for instance, the tautomer layer can be omitted if that type of information is not relevant to the
International Chemical Identifier
International_Chemical_Identifier
Chemical compound
pyrrole derivatives fused to a butadiene. In solutions, the 2H-isoindole tautomer predominates. It resembles a pyrrole more than a simple imine. The degree
Isoindole
Class of organic compounds
acid, the parent compound of the imidic acids. H2NCH2OH → HNCHOH + H2 (tautomer of formamide) Geminal amino alcohols with side chains similarly form imidic
Imidic_acid
Experimental antiviral drug with potential activity against RNA viruses
experimentally in some humans infected with the virus. The possible tautomerism of favipiravir has been investigated computationally and experimentally
Favipiravir
Chemical compound
many heterocycles, such as pyrazoles. It exists predominantly as the enol tautomer C6H5C(OH)=CHC(O)CH3. Its conjugate base (pKa=8.7) forms stable complexes
Benzoylacetone
Chemical compound
replaced by hydroxyl groups –OH; or any of its tautomers. The substance exists as an equilibrium of 17 tautomers that easily interconvert among each other
Cyameluric_acid
Chemical compound
The compound is often referred to as 2-mercaptoimidazole, which is a tautomer that is not observed. The compound forms a variety of metal complexes.
2-Imidazolidinethione
Organic compound
corresponding dione using aluminium powder at high temperature. Three tautomers of 1,4-thiazine exist as above. Methylene blue, contains a related ring
Thiazine
Chemical compound in DNA and RNA
adenosine diphosphate, and S-adenosylmethionine. Adenine forms several tautomers, compounds that can be rapidly interconverted and are often considered
Adenine
Chemical compound (H–N=C=O)
volatile and poisonous gas, condensing at 23.5 °C. It is the predominant tautomer and an isomer of cyanic acid (aka. cyanol) (H−O−C≡N), and the monomer of
Isocyanic_acid
Chemical compound
some interest because in its molten state, it exists mainly as the diketo tautomer. It can be prepared by reduction of 1,4-naphthoquinone with dithionite
1,4-Dihydroxynaphthalene
enediol structure is stabilized by the resonance resulting from the tautomerism with the adjacent carbonyl. Therefore, the chemical equilibrium produces
Reductone
Intermolecular attraction between a hydrogen donor-and-acceptor pair
shifts in the 1H NMR spectrum. For example, the acidic proton in the enol tautomer of acetylacetone appears at δ H {\displaystyle \delta _{\text{H}}} 15
Hydrogen_bond
Organic compound ((CH3)2CO); simplest ketone
(CH3)2C(OH)2 K = 10−3 M−1 Like most ketones, acetone exhibits the keto–enol tautomerism in which the nominal keto structure (CH3)2C=O of acetone itself is in
Acetone
Index of chemical compounds with the same molecular formula
unstable tautomer 1H-azirine, −CH=CH−NH−) Ethenimine (H2C=C=NH), an unstable tautomer of acetonitrile Ethynamine [wd] (HC≡C−NH2), another unstable tautomer of
C2H3N
Organic compound with the formula P(OR)3
the formula P(OR)3. They can be considered as esters of an unobserved tautomer phosphorous acid, H3PO3, with the simplest example being trimethylphosphite
Phosphite_ester
Chemical compound
being Pigment Yellow 74. Acetoacetanilide crystallizes as the keto-amide tautomer according to X-ray crystallography. The molecules are linked by intermolecular
Acetoacetanilide
Chemical compound
simplified) quinolones. 4-Quinolone exists in equilibrium with a minor tautomer, 4-hydroxyquinoline (CAS#611-36-9). Aside from pedagogical interest, 4-quinolone
4-Quinolone
Chemical compound
organic compound related structurally to quinoline. It is the majority tautomer in equilibrium with 2-quinolinol. The compound can be classified as a cyclic
2-Quinolone
Chemical compound
in 1995. The compound is well described by the formula H3NSO3, not the tautomer H2NSO2(OH). The relevant bond distances are 1.44 Å for the S=O and 1.77 Å
Sulfamic_acid
Chemical compound
Cyanamide exists as two tautomers, one with the connectivity N≡C–NH2 and the other with the formula HN=C=NH ("carbodiimide" tautomer). The N≡C–NH2 form dominates
Cyanamide
Chemical compound
(JSmol) Interactive image selenol tautomer: Interactive image ChEBI CHEBI:79071 ChemSpider 34449139 PubChem CID selenol tautomer: 86289064 InChI InChI=1S/C9H15N3O2Se/c1-12(2
Selenoneine
Hacac used for 1,3-diketones. These species can exist as a mixture of tautomers. Acetylacetone and related 1,3-diketones condense with primary alkyl-
NacNac
Appetite suppressant
(-ol) form in neutral media and undergoes protonation to the benzophenone tautomer in acidic media. QSAR studies have indicated that the ability of mazindol
Mazindol
Class of chemical compounds
(imine formation) Imines are tautomers of enamines. The enamine-imine tautomerism is analogous to the keto-enol tautomerism. Protonation of enamines occurs
Enamine
Anticoagulant medication
Acyclic tautomer (left) and cyclic hemiketal tautomer (right)
Warfarin
Organic compound
displays lactam–lactim tautomerism. Uric acid crystallizes in the lactam form, with computational chemistry also indicating that tautomer to be the most stable
Uric_acid
Chemical compound
2-hydroxypyridine converts significantly to the pyridone tautomer, the related imine tautomer (HNC5H4NH) is less important for 2-aminopyridine. 2-Aminopyridine
2-Aminopyridine
Chemical compound
structure which means it has three interconnected rings of atoms and is a tautomer of alloxazine. The structure is formed by primary-secondary aromatic o-diamines
Isoalloxazine
Chemical compound
attracted some interest because its conjugate base exists as the dionate tautomer: The pKa of 1,3-dihydroxynaphthalene is 7.35, which is anomalous compared
1,3-Dihydroxynaphthalene
Chemical compound
a dye precursor used in industry. The molecule can exist in different tautomers resulting in different crystalline solids. CID 18980 from PubChem Venkataraman
Diiminoisoindole
Chemical compound
well as a ketone. The compound exists in a chemical equilibrium with its tautomer 6-acetyl-1,2,3,4-tetrahydropyridine that differs only by the position of
6-Acetyl-2,3,4,5-tetrahydropyridine
6-Acetyl-2,3,4,5-tetrahydropyridine
Chemical compound
carbonous acid is a chemical compound with formula C(OH)2. It is an unstable tautomer of formic acid. There is no evidence that this compound exists in solution
Dihydroxymethylidene
Chemical compound
Acetoacetylation with diketene followed by diazo coupling. The ketohydrazone tautomer is shown.
Acetoacetamide
Class of organic compounds
pleconaril. The 1,2,3-isomer is unstable and ring-opens to form the diazoketone tautomer; however, it does exist within the unusual sydnone motif. In 2018, a compound
Oxadiazole
Breakdown product of creatine phosphate
HCl → C4H7N3O·HCl + H2O This produces creatinine hydrochloride. Several tautomers of creatinine exist; ordered by contribution, they are:
Creatinine
Chemical compound
crystallography, the molecule is nearly planar and exists as the keto-hydrazide tautomer. K. Hunger; W. Herbst (2012). "Pigments, Organic". Ullmann's Encyclopedia
Pigment_Yellow_12
Chemical compound
HN=C=N−C≡N, which is predicted to be slightly more stable than the symmetric tautomer dicyanimide [wd] N≡C−NH−C≡N. Dicyanamide was used as an anionic component
Dicyanamide
Chemical compounds with the same atoms but arranged and connected differently
skeletal isomers, positional isomers (or regioisomers), functional isomers, tautomers, and structural isotopomers. A skeletal isomer of a compound is a structural
Structural_isomer
Chemical compound of RNA
cyclic-amidic stability. The amide tautomer is referred to as the lactam structure, while the imidic acid tautomer is referred to as the lactim structure
Uracil
Method of finding chemicals in a database
in its alternative tautomer form. For histidine, it has been experimentally determined by 15N NMR spectroscopy that the 1-H tautomer is preferred over
Substructure_search
Chemical information database
count [HBAC], [HBACNT] • Hydrogen bond donor count [HBDC], [HBDCNT] • Tautomer count [TC], [TCNT], [TTMC] • Rotatable bond count [RBC], [RBCNT] • XLogP
PubChem
Chemical compound
depending on the preparation method, temperature, and presence of the thioenol tautomer. The polymer melts in the range of about 70 °C to 125 °C. Polymerization
Thioacetone
Substituted bicyclic heterocyclic compound derived from pteridine
range of tautomerism in water, beyond what is assumed by just keto-enol tautomerism. For the unsubstituted pterin, at least five tautomers are commonly
Pterin
Chemical compound
alkyne–alcohol (ynol) with the formula C2H2O or CHCHOH. It is the much-less-stable tautomer of ethenone. At low temperature in a solid argon matrix it is possible
Ethynol
Chemical compound
discovered. Sulfathiazole exists in various forms (polymorphs). The imine tautomer is dominant in solid samples. In the 1955 short story, Captive Audience
Sulfathiazole
Chemical compound
acedianthrone, a useful octacyclic pigment. Anthrone is the more stable tautomer relative to the anthrol as has been established also by X-ray crystallography
Anthrone
Chemical compound
explicable with reference to its tautomerism, which produces a small amount of the keto tautomer. One consequence of this tautomerism is the Bucherer reaction
2-Naphthol
Organic compounds with the general structure C=C–SH
thioenolates. These structures exhibit tautomerism to give thioketones or thioaldehydes, analogous to keto–enol tautomerism of carbonyl structures. Chiang, Yvonne;
Thioenol
Chemical compound
phosphorus compound with analogous stoichiometry exists as the tetrahedral tautomer. Similarly, organic derivatives such as phenylarsonic acid are tetrahedral
Arsonic_acid
Chemical compound
lighter members of main group elements than their heavier congeners. One tautomer of arsenous acid would have the formula HAsO(OH)2, called arsonic acid
Arsenous_acid
Chemical compound
Wireframe model of an eriochrome black T minor tautomer
Eriochrome_Black_T
Analytical technique
heteroaromatics because of the dramatic change in 15N shifts between tautomers. 15N NMR is also extremely valuable in protein NMR investigations. Most
Nitrogen-15 nuclear magnetic resonance spectroscopy
Nitrogen-15_nuclear_magnetic_resonance_spectroscopy
Principal curcuminoid of turmeric
are connected by two α,β-unsaturated carbonyl groups. It is a diketone tautomer, existing in enolic form in organic solvents and in keto form in water
Curcumin
Chemical compound
diphenylphosphine. Diphenylphosphine oxide exists in equilibrium with its minor tautomer diphenylphosphinous acid, ((C6H5)2POH: (C6H5)2P(O)H ⇌ (C6H5)2POH Diphenylphosphine
Diphenylphosphine_oxide
Chemical compound
Kekulé, skeletal formula of a 1-n-Butyl-3-methylimidazolium minor tautomer
C4mim
Chemical compound
the molecular formula C4H4O3. It interconverts between keto and enol tautomers: Many natural products such as ascorbic acid (vitamin C), penicillic acid
Tetronic_acid
Chemical compound
3-diketone, but the compound exists primarily as one of two equivalent enol tautomers. DBM is a white solid. Due UV-absorbing properties, derivatives of DBM
Dibenzoylmethane
Organic compounds with a diazoamino group
Triazenes derived from primary amines engage in tautomerism. In the case of symmetric triazenes, the tautomers are identical. Triazenes can be converted to
Triazenes
Chemical compound
both analgesic and antipyretic properties. Piroxicam exists as alkenol tautomer in organic solvents and as zwitterionic form in water. Piroxicam features
Piroxicam
Chemical compound
5-methylbenzotriazole, with small quantities of [their respective 7- and 6-methyl tautomers]". Synthesis is much like that of benzotriazole, but starting with
Tolyltriazole
Chemical compound
Benzotriazole features two fused rings. It can in principle exist as tautomers, but X-ray crystallography establishes the structure with hydrogen at
Benzotriazole
TAUTOMER
TAUTOMER
TAUTOMER
TAUTOMER
Surname or Lastname
English
English : metonymic occupational name for a needle maker from Old French aguillard, a variant (with a change of suffix) of aguillier, from a(i)guille ‘needle’.French : from Old French aguille ‘needle’ + the pejorative suffix -ard, hence a derogatory nickname for an irritating person.
Surname or Lastname
English
English : from a pet form of Dogge (see Dodge).
Girl/Female
Australian, Basque, French, Greek
Daughter of Oedipus
Girl/Female
American, Anglo, Australian, British, Christian, English, French, German, Scottish
Ardent; Wealthy; Female Version of Edwin; Prosperous Friend; The Capital City of Scotland
Boy/Male
Tamil
Lord Krishna
Girl/Female
Biblical
Opening, open.
Boy/Male
Hindu
Name of Lord Krishna
Girl/Female
Arabic, Muslim
Wealth; Riches
Boy/Male
Muslim
Brave
Male
Chinese
eastern sea.
TAUTOMER
TAUTOMER
TAUTOMER
TAUTOMER
TAUTOMER
n.
The condition, quality, or relation of metameric substances, or their respective derivatives, which are more or less interchangeable, according as one form or the other is the more stable. It is a special case of metamerism; thus, the lactam and the lactim compounds exhibit tautomerism.
a.
Relating to, or characterized by, tautomerism.