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Subdiscipline of chemistry
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. The
Stereochemistry
chemistry, dynamic stereochemistry studies the effect of stereochemistry on the reaction rate of a chemical reaction. Stereochemistry is involved in: stereospecific
Dynamic_stereochemistry
Representation method in chemistry
Unless all four substituents are explicit, this is true even when stereochemistry is being depicted using wedged or dashed bonds (see below). If all
Skeletal_formula
Graphic representation of a molecular structure
in skeletal formulas is indicated by the Natta projection method. Stereochemistry is used to show the relative spatial arrangement of atoms in a molecule
Structural_formula
Chemical group (–CH2–CH3)
In organic chemistry, an ethyl group (abbreviated as ET, Et or et) is an alkyl substituent with the formula −CH2CH3, derived from ethane (C2H6). Ethyl
Ethyl_group
Chemical coupling reaction
the oxaphosphetanes 4a and 4b. Under lithium-free conditions, the stereochemistry of the product 5 is due to the kinetically controlled addition of the
Wittig_reaction
Reductions with metal alkoxyaluminium hydrides are chemical reactions that involve either the net hydrogenation of an unsaturated compound or the replacement
Reductions with metal alkoxyaluminium hydrides
Reductions_with_metal_alkoxyaluminium_hydrides
Organometallic coupling reaction
The Grignard reaction (French: [ɡʁiɲaʁ]) is an organometallic chemical reaction in which, according to the classical definition, carbon alkyl, allyl, vinyl
Grignard_reaction
Chemical compound
Multistriatin is a pheromone of the elm bark beetle. It is a volatile compound released by a virgin female beetle when she has found a good source of food
Multistriatin
Chemical compound
Isoglutamine or α-glutamine is a gamma amino acid derived from glutamic acid by substituting the carboxyl group in position 1 with an amide group. This
Isoglutamine
Organic compound with a C=C–OH group
(1987-07-01). "Kinetic protonation of enols, enolates, and analogs. The stereochemistry of ketonization". Accounts of Chemical Research. 20 (7): 263–268. doi:10
Enol
Molecular-structural phenomenon
ISBN 978-0-8400-5444-9. Moss, G. P. (1996-01-01). "Basic terminology of stereochemistry (IUPAC Recommendations 1996)". Pure and Applied Chemistry. 68 (12):
Gauche_effect
Chemical reaction
Carbonyl oxidation with hypervalent iodine reagents involves the functionalization of the α position of carbonyl compounds through the intermediacy of
Carbonyl oxidation with hypervalent iodine reagents
Carbonyl_oxidation_with_hypervalent_iodine_reagents
Organic compound, provitamin
Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms, it is quickly
Panthenol
Chemical notation for the handedness of a chiral molecule or group
dextrorotatory and which is levorotatory. Rather, it indicates the compound's stereochemistry relative to that of the dextrorotatory or levorotatory enantiomer of
Absolute_configuration
Chemical compound
Reproterol is a short-acting β2 adrenoreceptor agonist used in the treatment of asthma. It was patented in 1965 and came into medical use in 1977. Reproterol
Reproterol
Skeletal muscle relaxant
Orphenadrine is an anticholinergic drug of the ethanolamine antihistamine class; it is closely related to diphenhydramine. It is a muscle relaxant that
Orphenadrine
Geometric property of some molecules and ions
type of inherent chirality. Chirality is an important concept for stereochemistry and biochemistry. Most substances relevant to biology are chiral, such
Chirality_(chemistry)
Fluorine reaction
Electrophilic fluorination is the combination of a carbon-centered nucleophile with an electrophilic source of fluorine to afford organofluorine compounds
Electrophilic_fluorination
Suffix used in organic chemistry
The suffix -ene is used in organic chemistry to form names of organic compounds where the -C=C- group has been attributed the highest priority according
-ene
Chemical compound
JWH-176 is an analgesic drug which acts as a cannabinoid receptor agonist. Its binding affinity at the CB1 receptor is 26.0 nM, making it more potent than
JWH-176
One of a pair of diastereomers
plural: epimera) in arthropod anatomy, see Pleuron (insect anatomy). In stereochemistry, an epimer is one of a pair of diastereomers. The two epimers have
Epimer
Nucleophilic addition of an allyl, allenyl or propargyl-stannane
Organostannane addition is reaction involving the nucleophilic addition of an allyl-, allenyl-, or propargyl-stannane to an aldehyde, imine, or (in rare
Organostannane_addition
Reactions of organocopper reagents involve species containing copper-carbon bonds acting as nucleophiles in the presence of organic electrophiles. Organocopper
Reactions of organocopper reagents
Reactions_of_organocopper_reagents
Chemical compound
Talinolol is a beta blocker. Talinolol contains a stereocenter and consists of two enantiomers. This is a racemate, i.e. a 1: 1 mixture of (R)- and the
Talinolol
Form of stereoisomerism in carbohydrates
which can be monitored by polarimetry. Monosaccharide nomenclature Stereochemistry Francis Carey (2000). Organic Chemistry (4th ed.). McGraw-Hill Higher
Anomer
Organic molecule containing two or more fused cyclobutane rings
In chemistry, a ladderane is an organic molecule containing two or more fused cyclobutane rings. The name arises from the resemblance of a series of fused
Ladderane
Chemical compound
Heme A (or haem A) is a heme, a coordination complex consisting of a macrocyclic ligand called a porphyrin, chelating an iron atom. Heme A is a biomolecule
Heme_A
Empirical rule in organic chemistry
therefore the most favored. The rule makes no generalizations about the stereochemistry of the newly formed alkene, but only the regiochemistry of the elimination
Zaytsev's_rule
Notation in organic chemistry for double bonds
stereochemistry of double bonds in organic chemistry. It is an extension of cis–trans isomer notation (which only describes relative stereochemistry)
E–Z_notation
Structures of cyclohexane
of pharmaceuticals. Eliel, Ernest Ludwig; Wilen, Samuel H. (2008). Stereochemistry of Organic Compounds. Wiley India. ISBN 978-8126515707. Smith, Michael
Cyclohexane_conformation
Class of lipids
Glycerophospholipids or phosphoglycerides are glycerol-based phospholipids. They are the main component of biological membranes in eukaryotic cells. They
Glycerophospholipid
Chemical reaction
Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide (N 2H 2)
Reductions_with_diimide
Medication used to treat absence seizures
Ethosuximide, sold under the brand name Zarontin among others, is a medication used to treat absence seizures. It may be used by itself or with other antiseizure
Ethosuximide
Chemical reaction
one (azaenolate A) with the stereochemistry of its C=C double bonds being E and that of its C-N bond being Z stereochemistry is dominant (EC=CZC-N) for
Enders SAMP/RAMP hydrazone-alkylation reaction
Enders_SAMP/RAMP_hydrazone-alkylation_reaction
Various molecular structures formed only by rotation about single bonds
the concept of asymmetric induction and the ability to predict the stereochemistry of reactions controlled by steric effects. [citation needed] In the
Rotamer
Chemical compound
Cadalane skeleton Cadinane stereochemistry Muurolane stereochemistry Amorphane stereochemistry Bulgarane stereochemistry A.-K. Borg-Karlson, T. Norin
Cadinene
Amphetamine-derived stimulant drug
Amfetaminil (also known as amphetaminil, N-cyanobenzylamphetamine, and AN-1; brand name Aponeuron) is a stimulant drug derived from amphetamine, which
Amfetaminil
American chemist
died in Chapel Hill, North Carolina. His research focussed on the stereochemistry and conformational analysis of flexible organic molecules, including
Ernest_L._Eliel
Stereoisomers that are nonsuperposable mirror images of each other
Chirality (physics) Diastereomer Dynamic stereochemistry Epimer Homochirality Molecular symmetry Stereochemistry Stereocenter "Enantiomer: Definition &
Enantiomer
Chemical compound
Thiobutabarbital (Inactin, Brevinarcon) is a short-acting barbiturate derivative invented in the 1950s. It has sedative, anticonvulsant and hypnotic effects
Thiobutabarbital
Microbial arene oxidation (MAO) refers to the process by which microbial enzymes convert aromatic compounds into more oxidized products. The initial intermediates
Microbial_arene_oxidation
Oxidation with chromium(VI) complexes involves the conversion of alcohols to carbonyl compounds or more highly oxidized products through the action of
Oxidation with chromium(VI) complexes
Oxidation_with_chromium(VI)_complexes
2017) was a German-born American organic chemist who specialized in stereochemistry. Born in Berlin on June 5, 1923, Mislow had moved to London by 1938
Kurt_Mislow
Antihypertensive drug of the calcium channel blocker class
Isradipine (tradenames DynaCirc, Prescal) is a calcium channel blocker of the dihydropyridine class. It is usually prescribed for the treatment of high
Isradipine
Anticoagulant medication
Warfarin, sold under the brand name Coumadin among others, is used as an anticoagulant medication. It is commonly used to prevent deep vein thrombosis
Warfarin
Chemical process
Synthesis of nucleosides involves the coupling of a nucleophilic, heterocyclic base with an electrophilic sugar. The silyl-Hilbert-Johnson (or Vorbrüggen)
Synthesis_of_nucleosides
Organic chemical transformations
Radical cyclization reactions are organic chemical transformations that yield cyclic products through radical intermediates. They usually proceed in three
Radical_cyclization
Antispasmodic drug
Trihexyphenidyl (THP, benzhexol, trihex, marketed as Artane and others) is an antispasmodic drug used to treat stiffness, tremors, spasms, and poor muscle
Trihexyphenidyl
Inhalational anesthesia medication
Desflurane (1,2,2,2-tetrafluoroethyl difluoromethyl ether), under the brand name Suprane, is a highly fluorinated methyl ethyl ether used for induction
Desflurane
Anti-arrhythmic medication
Propafenone, sold under the brand name Rythmol among others, is a class 1c anti-arrhythmic medication, which is used to treat illnesses associated with
Propafenone
Chemical compound
Cypenamine (INN, BAN), or cypenamine hydrochloride (USAN), also known as 2-phenylcyclopentylamine, is a psychostimulant drug which was developed by a group
Cypenamine
Organic anion formed by deprotonating a carbonyl (>C=O) compound
reaction conditions can control both the resulting enolate's regio- and stereochemistry. This provides one of the best understood synthetic strategies to introduce
Enolate
Chemical reaction
situ-generated epoxides. (4) The Payne rearrangement occurs with inversion of stereochemistry at C-2. Substrates containing multiple adjacent hydroxyl groups may
Payne_rearrangement
Chemical compound
α-Methyl-p-tyrosine (AMPT), or simply α-methyltyrosine, also known in its chiral 2-(S) form as metirosine, is a tyrosine hydroxylase enzyme inhibitor and
Α-Methyl-p-tyrosine
Synthetic pyrethroid used as insecticide
of the insecticidal activity is due to the proportion of absolute stereochemistry (1R) in the mixture. The active isomer of deltamethrin, (1R)-cis-3-(2
Cyhalothrin
Chemical compound
Bispidine (3,7-diazabicyclo[3.3.1]nonane) is an organic compound that is classified as a bicyclic diamine. Although synthetic, it is related structurally
Bispidine
Chemical compound
Beflubutamid is a chemical compound and amide. It is used in agriculture as a herbicide. Its chemical formula is C18H17F4NO2. Beflubutamid is used on arable
Beflubutamid
German chemist (1835–1902)
December 1902) was a German chemist, most famous for his work in early stereochemistry. The son of the radical Protestant theologian Gustav Wislicenus, Johannes
Johannes_Wislicenus
Substitution reaction with a carbocation intermediate
contrast to the SN2 mechanism, which is a stereospecific mechanism where stereochemistry is always inverted as the nucleophile comes in from the rear side of
SN1_reaction
Chemical compound
Terbutaline, sold under the brand names Bricanyl and Marex among others, is a β2 adrenergic receptor agonist, used as a "reliever" inhaler in the management
Terbutaline
Chemical reaction to produce organic compounds
The intramolecular Heck reaction (IMHR) in chemistry is the coupling of an aryl or alkenyl halide with an alkene in the same molecule. The reaction may
Intramolecular_Heck_reaction
1,2-migration of an alkyl or aryl group
The α-ketol rearrangement is the acid-, base-, or heat-induced 1,2-migration of an alkyl or aryl group in an α-hydroxy ketone or aldehyde to give an isomeric
Α-Ketol_rearrangement
Chemical species structure notation
to preserve the correct pairing. If stereochemistry is specified, adjustments must be made; see § Stereochemistry below. The one form of branch which
Simplified Molecular Input Line Entry System
Simplified_Molecular_Input_Line_Entry_System
Croatian-Swiss chemist (1906–1998)
received the 1975 Nobel Prize in chemistry for his research into the stereochemistry of organic molecules and reactions. Prelog was born, and spent his
Vladimir_Prelog
Chemical reaction
J. B. (1990). "An examination of the affect [sic] of the epoxide stereochemistry in the nitrogen extrusion from exo- and endo-6,7-diazo-3-oxotricyclo[3
Retro-Diels–Alder_reaction
Protein domain
epoxide attack. The reaction catalyzed by LEH results in selective stereochemistry at its chiral carbons. LEH affords pure enantiomers of the limonene-1
Limonene-1,2-epoxide hydrolase
Limonene-1,2-epoxide_hydrolase
Chemical compound
Nadic anhydride, also known as 5-norbornene-2,3-dicarboxylic anhydride, is an organic acid anhydride derivative of norbornene. Nadic anhydride exhibits
Nadic_anhydride
Antihypertensive drug of the calcium channel blocker class
Nitrendipine is a dihydropyridine calcium channel blocker. It is used in the treatment of primary (essential) hypertension to decrease blood pressure and
Nitrendipine
Molecule with a ring of bonded atoms
atoms with distinct substitution (by functional groups) such that stereochemistry and chirality of the compound results, including some manifestations
Cyclic_compound
Compound with a metal center bound to ligands
"Seven-coordination. A molecular orbital exploration of structure, stereochemistry, and reaction dynamics". Inorganic Chemistry. 16 (3): 511–522. doi:10
Coordination_complex
Antihypotensive medication
Midodrine, sold under the brand name Proamatine among others, is an antihypotensive medication used to treat orthostatic hypotension (low blood pressure
Midodrine
Organic acid found in many fruits
Tartaric acid is a white, crystalline organic acid that occurs naturally in many fruits, most notably in grapes but also in tamarinds, bananas, avocados
Tartaric_acid
Mechanism for nucleophilic substitution reactions
nucleophile such as dioxane two successive SN2 reactions take place and the stereochemistry is again retention. With standard SN1 reaction conditions the reaction
SNi
Chemical compound
of NOE correlations led the researchers to misassign the relative stereochemistry of the core stereotetrad. Moreover, as global absolute chemistry was
Kedarcidin
Non-selective beta blocker
Oxprenolol, sold under the brand name Trasicor among others, is a non-selective beta blocker with some intrinsic sympathomimetic activity. It was used
Oxprenolol
Organic chemical reaction
In organic chemistry, the Mallory reaction is a photochemical-cyclization–elimination reaction of diaryl-ethylene structures to form phenanthrenes and
Mallory_reaction
Chemical compound
Oxamniquine, sold under the brand name Vansil among others, is a medication used to treat schistosomiasis due to Schistosoma mansoni. Praziquantel, however
Oxamniquine
Chemical compound
groups (each at a methine chiral center), the structure's overall stereochemistry, and the N-methyl group all contribute to the toxicity of kalkitoxin
Kalkitoxin
Chemical compound
Menthone is a chemical compound of the monoterpene class of naturally occurring organic compounds found in a number of essential oils, one that presents
Menthone
Ability of a chemical reaction to produce an unequal mixture of stereoisomers
preferred relative stereochemistry. In this case, either two or more chiral centers are formed at once such that one relative stereochemistry is favored, or
Stereoselectivity
Antihypertensive drug of the calcium channel blocker class
Nimodipine, sold under the brand name Nimotop among others, is a calcium channel blocker used in preventing vasospasm secondary to subarachnoid hemorrhage
Nimodipine
Chemical reaction of three alkynes to form a benzene ring
An alkyne trimerisation is a [2+2+2] cycloaddition reaction in which three alkyne units (C≡C) react to form a benzene ring. The reaction requires a metal
Alkyne_trimerisation
Chemical compound
Alminoprofen is a non-steroidal anti-inflammatory drug. the non-proprietary name alminoprofen is derived from the compound's chemical name 2-(4-[{2-me
Alminoprofen
Chemical compound
history of coordination chemistry because of its stability and its stereochemistry. Many different salts have been described. The complex was first described
Tris(ethylenediamine)cobalt(III) chloride
Tris(ethylenediamine)cobalt(III)_chloride
Intramolecular reactions of diazocarbonyl compounds include addition to carbon–carbon double bonds to form fused cyclopropanes and insertion into carbon–hydrogen
Intramolecular reactions of diazocarbonyl compounds
Intramolecular_reactions_of_diazocarbonyl_compounds
Nonsteroidal anti-inflammatory drug
Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) that is used to relieve pain, fever, and inflammation. This includes painful menstrual periods
Ibuprofen
Antihypertensive drug of the calcium channel blocker class
Clevidipine (INN, trade name Cleviprex) is a dihydropyridine calcium channel blocker indicated for the reduction of blood pressure when oral therapy is
Clevidipine
Identifier for chemical substances
their bond connectivity, tautomeric information, isotope information, stereochemistry, and electronic charge information. Not all layers have to be provided;
International Chemical Identifier
International_Chemical_Identifier
Chemical compound
9))tridecane Identifiers CAS Number 100679-85-4 Y 3738-00-9 (unspecified stereochemistry) Y 3D model (JSmol) Interactive image ChEBI CHEBI:78307 ChEMBL ChEMBL496447 Y
Ambroxide
Chemical reaction
Asymmetric ester hydrolysis with pig liver esterase is the enantioselective conversion of an ester to a carboxylic acid through the action of the enzyme
Asymmetric ester hydrolysis with pig-liver esterase
Asymmetric_ester_hydrolysis_with_pig-liver_esterase
Dutch Nobel laureate in chemistry
organolithium reagents and organic photochemistry and stereochemistry. In the 1990s, Feringa's work in stereochemistry led to major contributions in photochemistry
Ben_Feringa
UV-B protectant used in sunscreens
Octyl methoxycinnamate or ethylhexyl methoxycinnamate (INCI) or octinoxate (USAN), trade names Eusolex 2292 and Uvinul MC80, is an organic compound that
Octyl_methoxycinnamate
French chemist (1847–1930)
Paris, France) was a French chemist. He is best known for his work in stereochemistry. Le Bel was educated at the École Polytechnique in Paris. In 1874 he
Joseph_Achille_Le_Bel
Chemical reaction
Vicinal difunctionalization refers to a chemical reaction involving transformations at two adjacent centers (most commonly carbons). This transformation
Vicinal_difunctionalization
Medication used for dementia
Donepezil, sold under the brand name Aricept among others, is a medication used to treat dementia of the Alzheimer's type. It appears to result in a small
Donepezil
Chemical reaction which forms a cyclic molecule
suprafacial-suprafacial (syn/syn stereochemistry) in most cases. Very few examples of antarafacial-antarafacial (anti/anti stereochemistry) reactions have also been
Cycloaddition
Polymerization after alignment of monomers by crystallisation
changing the alignment of the monomer within the crystal, the tacticity/stereochemistry of the polymer product could be easily controlled. An intuitive example
Topochemical_polymerization
Chemical compound
compound is also known as pinusenediol. The conformational structure and stereochemistry of serratenediol have been thoroughly researched using a combination
Serratenediol
Strychnos alkaloids are natural products primarily found in the seeds of the strychnine tree (Strychnos nux-vomica) and in the genus Catharanthus. The
Strychnos_alkaloids
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