List of chemical compounds with unusual names

Last updated

Chemical nomenclature, replete as it is with compounds with very complex names, is a repository for some names that may be considered unusual. A browse through the Physical Constants of Organic Compounds in the CRC Handbook of Chemistry and Physics (a fundamental resource) will reveal not just the whimsical work of chemists, but the sometimes peculiar compound names that occur as the consequence of simple juxtaposition. Some names derive legitimately from their chemical makeup, from the geographic region where they may be found, the plant or animal species from which they are isolated or the name of the discoverer.

Contents

Some are given intentionally unusual trivial names based on their structure, a notable property or at the whim of those who first isolate them. However, many trivial names predate formal naming conventions. Trivial names can also be ambiguous or carry different meanings in different industries, geographic regions and languages.

Godly noted that "Trivial names having the status of INN or ISO are carefully tailor-made for their field of use and are internationally accepted". [1] In his preface to Chemical Nomenclature, Thurlow wrote that "Chemical names do not have to be deadly serious". [2] A website in existence since 1997 [3] and maintained at the University of Bristol lists a selection of "molecules with silly or unusual names" strictly for entertainment. These so-called silly or funny trivial names (depending on culture) can also serve an educational purpose. In an article in the Journal of Chemical Education , Dennis Ryan argues that students of organic nomenclature (considered a "dry and boring" subject) may actually take an interest in it when tasked with the job of converting funny-sounding chemical trivial names to their proper systematic names. [4]

The collection listed below presents a sample of trivial names and gives an idea how chemists are inspired when they coin a brand new name for a chemical compound outside of systematic naming. It also includes some examples of systematic names and acronyms that accidentally resemble English words.

Elements

Glenn Seaborg told his students that he proposed the chemical symbol Pu (from P U) instead of the conventional "Pl" for plutonium as a joke, only to find it officially adopted. [5] Unununium (Uuu) was the former temporary name of the chemical element number 111, a synthetic transuranium element. This element was named roentgenium (Rg) in November 2004.

Compounds

Name based on shape

Barrelene
Barrelene Barrelene structure.png
Barrelene
C8H8, the name derives from the resemblance to a barrel. [6]
Basketane
Basketane Basketane-2D-skeletal-bold.png
Basketane
pentacyclo[4.4.0.02,5.03,8.04,7]decane (C10H12), a polycyclic alkane with a structure similar to a basket. [3]
Bowtiediene
Bowtiediene Spiropentadiene.png
Bowtiediene
Spiropentadiene, a polycyclic alkene with a 2D projection similar to a bowtie. [7]
Churchane
Churchane Churchane-2D-skeletal-bold.png
Churchane
A polycyclic alkane named "churchane" because it looks superficially like a church.
Cubane
Cubane Cuban.svg
Cubane
A hydrocarbon whose eight carbon atoms occupy the vertices of a cube. [8]
Dodecahedrane
Dodecahedrane Dodecahedrane-3D-vdW.png
Dodecahedrane
A Platonic hydrocarbon shaped like a dodecahedron. [9]
Fenestrane (Windowpane)
Fenestranes 4.4.4.4-fenestrane.png
Fenestranes
A class of compounds with a "window pane motif" (the name fenestrane derives from the Latin word fenestra, meaning window), comprising four fused carbocycles centred on a quaternary carbon resulting in a twice-over spiro compound. The illustration at right shows a generic fenestrane as well as the specific example [4,4,4,4]fenestrane. Fenestranes are of considerable interest in theoretical chemistry though comparatively few have actually been synthesised.
Housane
Housane.svg
A polycyclic alkane named "housane" because it looks superficially like a house. [3]
Ladderane
Pentacycloanammoxic Acid Pentacycloanammoxic acid.svg
Pentacycloanammoxic Acid
An organic molecule that looks like a ladder because it contains two or more fused rings of cyclobutane.
Nanokid
Nanokid.svg
Nanokids belongs to a series of NanoPutians, a series of organic molecules whose structural formula resemble human forms. "NanoPutian" is a portmanteau of nano-, a unit prefix meaning one billionth, and lilliputian, a fictional race of humans in the novel Gulliver's Travels by Jonathan Swift.

There are no chemical or practical uses for the NanoKid molecule or any of its known derivatives. However, James Tour has turned the NanoKid into a lifelike character to educate children in the sciences. It was found that 82% of students found that NanoKids made learning science more interesting and led to a 10–59% increase in understanding of the material presented. [10]

Olympiadane
Olympiadane Olympiadane.svg
Olympiadane
A mechanically-interlocked compound based on the topology for the Olympic rings.
Olympicene
Olympicene Olympicene.svg
Olympicene
Refers to the fused 5-benzene rings (C19H12), which is reminiscent of the Olympic Flag. [11]
Paddlanes
Paddlane General paddlane.svg
Paddlane
Paddlanes are bicyclic molecules that resemble the paddles on steamboats.
Penguinone
Penguinone Penguinone.svg
Penguinone
3,4,4,5-tetramethylcyclohexa-2,5-dienone; a two-dimensional representation of its structure resembles a penguin.
Pterodactylane
Pterodactylane Pterodactylane flying.png
Pterodactylane
[4]-ladderanes with substituents on the central rung. So named for their resemblance to a Pterodactyl. [12]
Prismane
Prismane Prismane-stick.png
Prismane
An isomer of benzene with the carbon atoms arranged in the shape of a triangular prism.
Propellanes
[1.1.1]Propellane 1.1.1-propellane.svg
[1.1.1]Propellane
Propellanes are bicyclic molecules that resemble propellers.
Quadratic acid
Squaric acid Squaric acid.svg
Squaric acid
A square-shaped organic compound, also called squaric acid.
Sulflower
Sulflower Sulflower-from-xtal-3D-vdW.png
Sulflower
A stable heterocyclic octacirculene based on thiophene, named as a portmanteau of sulfur and sunflower .
Volleyballene
Volleyballene.gif
Molecule composed of 60 carbon and 20 scandium atoms, which has an appearance similar to that of a volleyball.

Named after people

Buckminsterfullerene (Fullerene)
Fullerene C60 Molecule.svg
Fullerene
Also called the buckyball, this is an allotrope of carbon named after Richard Buckminster Fuller due to its resemblance to Fuller's geodesic domes. The term was coined by Harold Kroto. [13] The alternative name footballene was coined by A.D.J. Haymet [14] because the molecule also resembles a football; [3] the 70-atom version is said to resemble a rugby ball from its own oval shape.
Bullvalene
Bullvalene C10H10 Bullvalene.svg
Bullvalene C10H10
(tricyclo[3.3.2.02,8]deca-3,6,9-triene) (C10H10), was named by organic chemist Maitland Jones Jr. for William "Bull" Doering who predicted its properties in 1963. [15] [16] Within a specific temperature range the molecule is subject to rapid degenerate Cope rearrangements with the result that all carbon atoms and hydrogen atoms are equivalent and that none of the carbon–carbon bonds is permanent.
Dickite ( Al 2 Si 2O5(OH)4), a clay-like material with a number of manufacturing uses, one of which is as a coating for high-quality bond paper. It is named after its discoverer, Allan Brugh Dick. [17]
Josiphos ligands A well-known catalyst, named after Josi Puleo, the technician who first prepared it. [18] Mandyphos and Taniaphos also exist.
Welshite

A mineral named after the US amateur mineralogist Wilfred R. Welsh. Its formula is Ca2SbMg4FeBe2Si4O20.

Named after fictional characters

Alcindoromycine An anthracycline antibiotic agent named after the character Alcindoro in La Bohème . [19]
Bohemamine An anti-tumour agent named after the Puccini opera La Bohème . [19]
Collinemycin An anthracycline antibiotic agent named after the character Colline in La Bohème . [19]
Ranasmurfin A blue protein from the foam nests of a tropical frog, named after the Smurfs.
Mimimycin An anthracycline antibiotic agent named after the character Mimì in La Bohème . [19]
Musettamycin An anthracycline antibiotic agent named after the character Musetta in La Bohème . [19]
Marcellomycin An anthracycline antibiotic agent named after the character Marcello in La Bohème . [19]
Pikachurin A retinal protein named after Pokémon character / species Pikachu
Rudolphomycin An anthracycline antibiotic agent named after the character Rodolfo (Rudolph) in La Bohème . [19] [20]
Sonic hedgehog A protein named after Sonic the Hedgehog
Arsole
Arsole Arsole.png
Arsole
(C4H5 As), an analogue of pyrrole in which an arsenic atom replaces the nitrogen atom. [21] The aromaticity of arsoles has been debated for many years. [22] The compound in which a benzene ring is fused to arsole — typically on the carbon atoms 3 and 4 — is known as benzarsole. [3]
Cumene (C9H12), an aromatic hydrocarbon used in the production of phenol and acetone.
Cummingtonite ((Mg,Fe2+)2(Mg,Fe2+)5Si8O22(OH)2), a magnesium-iron silicate hydroxide, first identified in Cummington, Massachusetts. [3]
FAPTris(pentafluoroethyl)trifluorophosphate, an anion used in some ionic liquids. [23]
Fornacite A rare lead, copper chromate arsenate hydroxide mineral (Pb2CuCrO4AsO4OH), named after its discoverer, Lucien Lewis Forneau. [3]
Fucitol
L-Fucitol L-Fucitol chemical structure.png
L-Fucitol
(C6H14O5), an alcohol derived from Fucus vesiculosus , a North Atlantic seaweed. Its optical isomers are also called D-fuc-ol and L-fuc-ol. [3]
FucK The name of the gene that encodes L-fuculokinase, an enzyme that catalyzes a chemical reaction between L-fuculose, ADP, and L-fuculose-1-phosphate. [3]
Fukalite ( Ca 4 Si 2O6(CO3)(OH, F))2, a rare form of calcium silicocarbonate discovered in the Fuka Mine of Takahashi, Japan. [3]
Orotic acid
Orotic acid Orotic acid.svg
Orotic acid
Pyrimidinecarboxylic acid has been referred to as vitamin B13. Often misspelled "erotic acid". [3]
Pizda
Pizda Pizda.svg
Pizda
Abbreviated ligand name of a substance 1-(2’’-hydroxyl cyclohexyl)-3-[aminopropyl]-4-[3’-aminopropyl] piperazine, first synthesized by a group of Australian chemists. In Romanian and some Slavic languages, the word pizda is a vulgarism for "vagina" (see Reconstruction:Proto-Slavic/pizda).
Rhamnetin
Rhamnetin Rhamnetin.svg
Rhamnetin
A flavonol dye derived from buckthorn (rhamnus). [24]
SEX
SEX Sodium-ethylxanthate-2D-skeletal.png
SEX
An abbreviation of sodium ethyl xanthate, [25] a flotation agent used in the mining industry.
Spermine,
Spermidine
Spermine Spermine.svg
Spermine
Spermidine Spermidine-2D-skeletal.svg
Spermidine
growth factors involved in cellular metabolism. [3]
BARF
BARF BArF-3D-sticks.png
BARF
(tetrakis[3,5-bis(trifluoromethyl)phenyl]borate), a fluoroaryl borate B(Ar(CF3)2)4, used as a non-coordinating anion [26]
catP The name of the enzyme responsible for chloramphenicol resistance in various species of bacteria.
Constipatic acid
Constipatic acid Constipatic acid.svg
Constipatic acid
[2-(14-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid], an aliphatic acid derived from the Australian Xanthoparmelia lichen. [3] [27]
Crapinon An anticholinergic drug, one side effect of which is constipation. [3]
Diurea
Methylene diurea Methylene diurea.svg
Methylene diurea
Organic compounds containing two urea moieties. Specific examples include methylene diurea and ethylene diurea.
dUMP
dUMP DUMP chemical structure.png
dUMP
Deoxyuridine monophosphate, an intermediate in nucleotide metabolism
Earthcide,
or Fartox
Some of the many names for pentachloronitrobenzene, a fungicide. [28]
Nonanal
Nonanal Nonanal.png
Nonanal
(C9H18O), an aldehyde derived from nonane. [29]
PoOChemical formula of polonium monoxide.
Uranate The chemical term for an oxyanion of the element uranium. [3]
Vomitoxin
Vomitoxin Deoxynivalenol.png
Vomitoxin
A mycotoxin occurring in grains. [3]
Cadaverine
Cadaverine Pentane-1,5-diamine 200.svg
Cadaverine
A foul-smelling diamine produced by putrefaction of dead animal tissue. [3] [30]
DEAD, DEADCAT
DEAD DEAD.svg
DEAD
Diethyl azodicarboxylate: An apt acronym, given that diethyl azodicarboxylate is explosive; shock sensitive; carcinogenic; and an eye, skin, and respiratory irritant. [3]
Earthcide,
or Fartox
Some of the many names for pentachloronitrobenzene, a fungicide. [31]
Putrescine
Putrescine Diaminobutane.svg
Putrescine
A foul-smelling diamine produced by the putrefaction of dead animal tissue. [3]
Angelic acid
Angelic acid Angelic acid.png
Angelic acid
An organic acid found in garden angelica ( Angelica archangelica ), Umbelliferae, and many other plants.
DAMN
DAMN Structure.png
Diaminomaleonitrile, a cyanocarbon that contains two amine groups and two nitrile groups bound to an ethylene backbone.
Diabolic acid A series of long-chain dicarboxylic acids with chains of different lengths. Named after the Greek word diabollo meaning to mislead. [32]
Draculin An anticoagulant found in the saliva of vampire bats. [33]
Vitamin C (Godnose)Albert Szent-Gyorgyi coined the term "ignose" to describe ascorbic acid, which he isolated and published. When the journal's editor refused to accept ignose as a plausible name, Szent-Gyorgyi suggested 'Godnose' (a joke meaning that only God could know the real identity of the molecule). The editor suggested that the name be changed to something more formal. [34]
Luciferase A generic term for the class of oxidative enzymes that produce bioluminescence.
Lucifer yellow Lucifer Yellow is a food coloring that is commonly found in hot sauces such as salsa pickle. Because it fluoresces under ultraviolet light and stains certain regions between plant cells, it's also used in plant microscopy anatomy studies.
Miraculin A glycoprotein found in miracle fruit that makes sour foods taste sweet after contact with taste buds. [35]

Sounds like a name (person, brand or organization)

Adamantane
Adamantane Adamantane.svg
Adamantane
(tricyclo[3.3.1.13,7]decane), a crystalline cycloalkane, [36] [37] an isomer of twistane. Name resembles that of English pop star Adam Ant. [3]
Irene Hantzsch-Widman nomenclature for a monocyclic, heterocyclic compound with three ring atoms. [38]
Naftazone(C11H9N3O2), a vasoprotective drug. The NAFTA free-trade zone is the area covered by the North American Free Trade Agreement. [39]
PEPPSI Pyridine-Enhanced Precatalyst Preparation Stabilization and Initiation. [40]

A part sounds like an English word

Antipain Antipain works as a protease inhibitor, preventing proteins from being degraded. It is a highly toxic compound that, ironically, causes severe itching or pain when it comes into contact with the skin. Because it inhibits the action of papain, an enzyme found in papayas, its name is actually an abbreviation of anti-papain.
Bongkrek acid
Bongkrek acid Bongkrekic acid.svg
Bongkrek acid
Name sounds like a combination of English words related to recreational drugs: bong ; crack , a preparation of cocaine; and acid, a street name for lysergic acid diethylamide.
Constipatic Acid Some Australian lichens, like Parmelia constipata, have this as a component. Protoconstipatic acid, dehydroconstipatic acid, and methyl constipatate are all constipatic acid derivatives.
DiNOsarCommon shortening of di-nitro sarcophagine. Used due to shorter length compared to the IUPAC name of 1,8-dinitro-3,6,10,13,16,19-hexaazabicyclo[6.6.6]icosane. Sounds similar to the word dinosaur
GardeninGardenins, which are flavones extracted from the Indian plant Gardenia lucida , come in a variety of forms.
Hirsutene
Hirsutene Hirsutene.png
Hirsutene
[41] [42] Is also named after an animal, a goat (Hircus).
Magic acid A superacid consisting of a mixture, most commonly in a 1:1 molar ratio, of fluorosulfuric acid (HSO3F) and antimony pentafluoride (SbF5).
Megaphone A ketone derived from the root of Aniba megaphylla . [43]
Melon A compound consisting mostly of linked heptazine units with an undetermined composition.
Melon Melon structure unit Komatsu.png
Melon
Mispickel An older name for the mineral arsenopyrite, an iron arsenic sulfide and major source of the element arsenic, sounds like 'miss pickle'. From German. [44]
Moronic acid
Moronic acid Moronic acid structure.png
Moronic acid
[3-oxoolean-18-en-28-oic acid], a natural triterpene
Performic acid A strongly oxidizing acid related to formic acid.
Noggin A signalling protein involved in embryonic development.
Nonose A monosaccharide with nine carbons. An example is sialic acid.
Periodic acid
Periodic acid Orthoperiodic-acid-3D-balls.png
Periodic acid
Or per-iodic acid, is pronounced /ˌpɜːrˈɒdɪk/ PURR-eye-OD-ik and not * /ˌpɪəriˈɒdɪk/ PEER-ee-OD-ik. It refers to one of two interconvertible species: HIO4 (metaperiodic acid), or H5IO6 (orthoperiodic acid – illustrated at right). The per- prefix in the name denotes that iodine is present in its highest possible (+VII) oxidation state.
Picket Fence Porphyrin (5,10,15,20-tetrakis(alpha,alpha,alpha-2-pivalamidophenyl)porphyrin), used to model heme enzyme active sites.
Piranha solution A strongly oxidizing mixture of hydrogen peroxide and sulfuric acid used to remove organic residues from substrates and glassware. The name refers to the voracious appetite of the Amazonian piranha fish.
Rednose A sugar derived from the degradation of rudolphomycin. [19]
Rhamnose
Rhamnose Alpha-L-Rhamnopyranose.svg
Rhamnose
A sugar naturally occurring in buckthorn (rhamnus).
Ru(Tris)BiPy-on-a-stickShorthand form of (trans-1,4-bis[(4-pyridyl)ethenyl]benzene)(2,2'-bipyridine)ruthenium(II). [45]
Traumatic acid
Traumatic acid Traumatic acid structure.png
Traumatic acid
A substance occurring in plants, with a role in healing damaged tissue.

Other

Bastardane A close relative to tetramantane (a higher homologue of adamantane), its proper name is nonacyclo[11.7.1.112,18.03,16.04,13.05,10.06,14.07,11.015,20]docosane. Because its unusual ethano-bridge was a deviation from the standard hydrocarbon caged rearrangements, it came to be known as bastardane—the unwanted child. [3] [46]
Dinocap
Dinocap Dinocap-4 v2.png
Dinocap
(C18H24N2O6), a miticide and contact fungicide used to control powdery mildew in crops.
DuPhos
DuPhos DuPhos ligands.svg
DuPhos
A class of asymmetric ligands for asymmetric synthesis. The name DuPhos is derived from the chemical company that developed this type of ligand (DuP, DuPont) and the compound class of phospholanes (Phos) it belongs to.
FOOF
Fluorine dioxide.svg
Dioxygen difluoride, O2F2, an extremely unstable compound which reacts explosively with most other substances – the nickname "FOOF" is a play on its formula. [47]
Furfuryl furfurate The name of the molecule is difficult to say fast. It has a strong odor and can be used as a polymerization inhibitor in the vapor phase. Its name is derived from the Latin word "furfur," which means "bran" (the source of the compound). Furfural alcohol, a related molecule, is reportedly used in the fabrication of the Reinforced Carbon-Carbon (RCC) sections used in the space shuttle.
Gossypol
Gossypol Gossypol.png
Gossypol
A toxin found in cottonseed used as a male oral contraceptive. [3]
Methionylthreonylthreonylglutaminylarginyl...isoleucine The IUPAC name for Titin. This is the largest known protein and so has the longest chemical name. Written in full, it contains 189,819 letters. [48]
Periplanone B
Periplanone B Periplanone B.png
Periplanone B
A pheromone of the female American cockroach.
Thebacon
Thebacon Dihydrocodeinone enol acetate.png
Thebacon
Dihydrocodeinone enol acetate, an opioid analgesic or antitussive. [ citation needed ]

See also

Related Research Articles

<span class="mw-page-title-main">Allenes</span> Any organic compound containing a C=C=C group

In organic chemistry, allenes are organic compounds in which one carbon atom has double bonds with each of its two adjacent carbon atoms. Allenes are classified as cumulated dienes. The parent compound of this class is propadiene, which is itself also called allene. A group of the structure R2C=C=CR− is called allenyl, while a substituent attached to an allene is referred to as an allenic substituent. In analogy to allylic and propargylic, a substituent attached to a saturated carbon α to an allene is referred to as an allenylic substituent. While allenes have two consecutive ('cumulated') double bonds, compounds with three or more cumulated double bonds are called cumulenes.

In chemistry, an inorganic compound is typically a chemical compound that lacks carbon–hydrogen bonds⁠that is, a compound that is not an organic compound. The study of inorganic compounds is a subfield of chemistry known as inorganic chemistry.

Cubane is a synthetic hydrocarbon compound with the formula C8H8. It consists of eight carbon atoms arranged at the corners of a cube, with one hydrogen atom attached to each carbon atom. A solid crystalline substance, cubane is one of the Platonic hydrocarbons and a member of the prismanes. It was first synthesized in 1964 by Philip Eaton and Thomas Cole. Before this work, Eaton believed that cubane would be impossible to synthesize due to the "required 90 degree bond angles". The cubic shape requires the carbon atoms to adopt an unusually sharp 90° bonding angle, which would be highly strained as compared to the 109.45° angle of a tetrahedral carbon. Once formed, cubane is quite kinetically stable, due to a lack of readily available decomposition paths. It is the simplest hydrocarbon with octahedral symmetry.

<span class="mw-page-title-main">Organolithium reagent</span> Chemical compounds containing C–Li bonds

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers. They have also been applied in asymmetric synthesis in the pharmaceutical industry. Due to the large difference in electronegativity between the carbon atom and the lithium atom, the C−Li bond is highly ionic. Owing to the polar nature of the C−Li bond, organolithium reagents are good nucleophiles and strong bases. For laboratory organic synthesis, many organolithium reagents are commercially available in solution form. These reagents are highly reactive, and are sometimes pyrophoric.

<span class="mw-page-title-main">Chirality (chemistry)</span> Geometric property of some molecules and ions

In chemistry, a molecule or ion is called chiral if it cannot be superposed on its mirror image by any combination of rotations, translations, and some conformational changes. This geometric property is called chirality. The terms are derived from Ancient Greek χείρ (cheir) 'hand'; which is the canonical example of an object with this property.

<span class="mw-page-title-main">Adamantane</span> Molecule with three connected cyclohexane rings arranged in the "armchair" configuration

Adamantane is an organic compound with formula C10H16 or, more descriptively, (CH)4(CH2)6. Adamantane molecules can be described as the fusion of three cyclohexane rings. The molecule is both rigid and virtually stress-free. Adamantane is the most stable isomer of C10H16. The spatial arrangement of carbon atoms in the adamantane molecule is the same as in the diamond crystal. This similarity led to the name adamantane, which is derived from the Greek adamantinos (relating to steel or diamond). It is a white solid with a camphor-like odor. It is the simplest diamondoid.

<span class="mw-page-title-main">Prismane</span> Chemical compound

Prismane or 'Ladenburg benzene' is a polycyclic hydrocarbon with the formula C6H6. It is an isomer of benzene, specifically a valence isomer. Prismane is far less stable than benzene. The carbon (and hydrogen) atoms of the prismane molecule are arranged in the shape of a six-atom triangular prism—this compound is the parent and simplest member of the prismanes class of molecules. Albert Ladenburg proposed this structure for the compound now known as benzene. The compound was not synthesized until 1973.

<span class="mw-page-title-main">Polyyne</span> Any organic compound with alternating C–C and C≡C bonds

A polyyne is any organic compound with alternating single and triple bonds; that is, a series of consecutive alkynes, (−C≡C−)n with n greater than 1. These compounds are also called polyacetylenes, especially in the natural products and chemical ecology literature, even though this nomenclature more properly refers to acetylene polymers composed of alternating single and double bonds (−CR=CR′−)n with n greater than 1. They are also sometimes referred to as oligoynes, or carbinoids after "carbyne" (−C≡C−), the hypothetical allotrope of carbon that would be the ultimate member of the series. The synthesis of this substance has been claimed several times since the 1960s, but those reports have been disputed. Indeed, the substances identified as short chains of "carbyne" in many early organic synthesis attempts would be called polyynes today.

<span class="mw-page-title-main">Organozinc chemistry</span>

Organozinc chemistry is the study of the physical properties, synthesis, and reactions of organozinc compounds, which are organometallic compounds that contain carbon (C) to zinc (Zn) chemical bonds.

<span class="mw-page-title-main">Sandwich compound</span> Chemical compound made of two ring ligands bound to a metal

In organometallic chemistry, a sandwich compound is a chemical compound featuring a metal bound by haptic, covalent bonds to two arene (ring) ligands. The arenes have the formula CnHn, substituted derivatives and heterocyclic derivatives. Because the metal is usually situated between the two rings, it is said to be "sandwiched". A special class of sandwich complexes are the metallocenes.

<span class="mw-page-title-main">Dewar benzene</span> Chemical compound

Dewar benzene (also spelled dewarbenzene) or bicyclo[2.2.0]hexa-2,5-diene is a bicyclic isomer of benzene with the molecular formula C6H6. The compound is named after James Dewar who included this structure in a list of possible C6H6 structures in 1869. However, he did not propose it as the structure of benzene, and in fact he supported the correct structure previously proposed by August Kekulé in 1865.

The Kulinkovich reaction describes the organic synthesis of substituted cyclopropanols through reaction of esters with dialkyl­dialkoxy­titanium reagents, which are generated in situ from Grignard reagents containing a hydrogen in beta-position and titanium(IV) alkoxides such as titanium isopropoxide. This reaction was first reported by Oleg Kulinkovich and coworkers in 1989.

ChemSpider is a freely accessible online database of chemicals owned by the Royal Society of Chemistry. It contains information on more than 100 million molecules from over 270 data sources, each of them receiving a unique identifier called ChemSpider Identifier.

Trimethylarsine (abbreviated TMA or TMAs) is the chemical compound with the formula (CH3)3As, commonly abbreviated AsMe3 or TMAs. This organic derivative of arsine has been used as a source of arsenic in microelectronics industry, a building block to other organoarsenic compounds, and serves as a ligand in coordination chemistry. It has distinct "garlic"-like smell. Trimethylarsine had been discovered as early as 1854.

<span class="mw-page-title-main">1,2-Bis(dimethylarsino)benzene</span> Chemical compound

1,2-Bis(dimethylarsino)benzene (diars) is the organoarsenic compound with the formula C6H4(As(CH3)2)2. The molecule consists of two dimethylarsino groups attached to adjacent carbon centers of a benzene ring. It is a chelating ligand in coordination chemistry. This colourless oil is commonly abbreviated "diars."

<span class="mw-page-title-main">Basketane</span> Chemical compound

Basketane is a polycyclic alkane with the chemical formula C10H12. The name is taken from its structural similarity to a basket shape. Basketane was first synthesized in 1966, independently by Masamune and Dauben and Whalen. A patent application published in 1988 used basketane, which is a hydrocarbon, as a source material in doping thin diamond layers because of the molecule's high vapor pressure, carbon ring structure, and fewer hydrogen-to-carbon bond ratio.

In organic chemistry, diazirines are a class of organic molecules consisting of a carbon bound to two nitrogen atoms, which are double-bonded to each other, forming a cyclopropene-like ring, 3H-diazirine. They are isomeric with diazocarbon groups, and like them can serve as precursors for carbenes by loss of a molecule of dinitrogen. For example, irradiation of diazirines with ultraviolet light leads to carbene insertion into various C−H, N−H, and O−H bonds. Hence, diazirines have grown in popularity as small, photo-reactive, crosslinking reagents. They are often used in photoaffinity labeling studies to observe a variety of interactions, including ligand-receptor, ligand-enzyme, protein-protein, and protein-nucleic acid interactions.

<span class="mw-page-title-main">RTI-274</span> Chemical compound

RTI(-4229)-274, or 2β-( methyl)-3α-(4-fluorophenyl)​nortropane is a phenyltropane homologue of paroxetine developed by the group led by F Ivy Carroll in the 1990s.

<span class="mw-page-title-main">Dynamic combinatorial chemistry</span>

Dynamic combinatorial chemistry (DCC); also known as constitutional dynamic chemistry (CDC) is a method to the generation of new molecules formed by reversible reaction of simple building blocks under thermodynamic control. The library of these reversibly interconverting building blocks is called a dynamic combinatorial library (DCL). All constituents in a DCL are in equilibrium, and their distribution is determined by their thermodynamic stability within the DCL. The interconversion of these building blocks may involve covalent or non-covalent interactions. When a DCL is exposed to an external influence, the equilibrium shifts and those components that interact with the external influence are stabilised and amplified, allowing more of the active compound to be formed.

In organic chemistry, the Lombardo methylenation is a name reaction that allows for the methylenation of carbonyl compounds with the use of Lombardo's reagent, which is a mix of zinc, dibromomethane, and titanium tetrachloride.

References

  1. Godly, E.W. (1998). Chemical Nomenclature. Kluwer Academic Publishers. p. 20. ISBN   978-0-7514-0475-3.
  2. Thurlow, Kevin (1998). Chemical Nomenclature. Kluwer Academic Publishers. xii. ISBN   978-0-7514-0475-3.
  3. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 May, Paul (28 May 2013). "Molecules with Silly or Unusual Names". Bristol University. Retrieved 1 November 2013.
  4. Ryan, Dennis (1997). "Old MacDonald Named a Compound: Branched Enynenynols" (PDF). Journal of Chemical Education. 74 (7): 782. Bibcode:1997JChEd..74..782R. doi:10.1021/ed074p782 . Retrieved 2007-08-16.[ permanent dead link ]
  5. Glenn T. Seaborg, Citizen-Scholar Archived 2020-11-14 at the Wayback Machine , By Peggy House, Reprinted from The Seaborg Center Bulletin, April 1999
  6. Zimmerman, Howard E.; Robert M. Paufler (1960). "Bicyclo [2.2.2]octa-2,5,7-triene (barrelene), a unique cyclic six electron pi system". Journal of the American Chemical Society . 82 (6): 1514–1515. doi:10.1021/ja01491a071.
  7. "Elusive bowtie pinned down - synthesis of spiropentadiene, a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie". Science News. July 13, 1991.
  8. Verbrugge, P. A. (1977). "Unusual organic compounds. XXIV. Compounds with the formula (CH)n. (d). Synthesis of cubane, (CH)8; homocubanes". Chemie en Techniek (Amsterdam). 32 (4): 120–123.
  9. Pubchem. "Dodecahedrane". pubchem.ncbi.nlm.nih.gov. Retrieved 2018-07-28.
  10. "NanoKids - Mission". 2007. Archived from the original on 2016-08-19. Retrieved February 21, 2023.
  11. "'Olympic rings' molecule olympicene in striking image". BBC Online . 27 May 2012. Retrieved 28 May 2012.
  12. Horst, Matías; Meisner, Jan; Yang, Jinghui; Kouznetsova, Tatiana B.; Craig, Stephen L.; Martínez, Todd J.; Xia, Yan (2024-01-10). "Mechanochemistry of Pterodactylane". Journal of the American Chemical Society. 146 (1): 884–891. doi:10.1021/jacs.3c11293. ISSN   0002-7863. PMID   38131266.
  13. Kroto, H.W.; Heath, J.R.; O'Brien, S.C.; Curl, R.F.; Smalley, R.E. (1985). "C60: Buckminsterfullerene". Nature. 318 (6042): 162. Bibcode:1985Natur.318..162K. doi:10.1038/318162a0. S2CID   4314237.
  14. Haymet, A.D.J. (1986). "Footballene: a theoretical prediction for the stable, truncated icosahedral molecule C60". J. Am. Chem. Soc. 108 (2): 319. doi:10.1021/ja00262a035.
  15. Doering, W. von E.; Roth, W. R. (1963). "A Rapidly Reversible Degenerate Cope Rearrangement : Bicyclo[5.1.0]octa-2,5-diene". Tetrahedron . 19 (5): 715–737. doi:10.1016/S0040-4020(01)99207-5.[ dead link ]
  16. Ault, Addison (2001). "The Bullvalene Story. The Conception of Bullvalene, a Molecule That Has No Permanent Structure". J. Chem. Educ. 78 (7): 924. Bibcode:2001JChEd..78..924A. doi:10.1021/ed078p924.
  17. Ross, C.; Kerr, P.F. (1931). "Dickite, a Kaolin Mineral" (PDF). American Mineralogist. 15: 34–39.
  18. Blaser, Hans-Ulrich; Brieden, Walter; Pugin, Benoit; Spindler, Felix; Studer, Martin; Togni, Antonio (2002). "Solvias Josiphos ligands: from discovery to technical applications". Topics in Catalysis. 19 (1): 3–16. doi:10.1023/A:1013832630565. S2CID   95738043.
  19. 1 2 3 4 5 6 7 8 Nettleton DE Jr, Balitz DM, Doyle TW, Bradner WT, Johnson DL, O'Herron FA, Schreiber RH, Coon AB, Moseley JE, Myllymaki RW, J Nat Prod. 1980 Mar–Apr;43(2):242–258. DOI: 10.1021/np50008a003
  20. "Canadian Patents Database CA 1110562: Anthracycline antibiotic designated RUDOLPHOMYCIN". Archived from the original on 2007-11-14. Retrieved 2007-08-16.
  21. G. Märkl & H. Hauptmann (1983-06-14). "Untersuchungen zur Chemie der Arsole 1,1-dichlor-1-R-λ5-arsole-1-chlorarsole 2,2′,5,5′-tetraphenyldiarsolyl (Studies on the chemistry of arsoles)". J. Organomet. Chem. 248 (3): 269–285. doi:10.1016/S0022-328X(00)98709-6.
  22. Mikael P. Johansson & Jonas Jusélius (2005). "Arsole Aromaticity Revisited". Lett. Org. Chem. (3): 469–474.
  23. Ignat’ev, N.V.; Welz-Biermann, U.; Kucheryna, A.; Bissky, G.; Willner, H. (2005). "New ionic liquids with tris(perfluoroalkyl)trifluorophosphate (FAP) anions". Journal of Fluorine Chemistry. 126 (8): 1150–1159. Bibcode:2005JFluC.126.1150I. doi:10.1016/j.jfluchem.2005.04.017.
  24. Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
  25. See, for example, Okibe, N; Johnson, DB (2004). "Toxicity of flotation reagents to moderately thermophilic bioleaching microorganisms". Biotechnology Letters. 24 (23): 2011–2016. doi:10.1023/A:1021118915720. S2CID   23948075.
  26. "BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013.
  27. Chester, DO (1979). "Three New Aliphatic Acids from Lichens of Genus Parmelia (Subgenus Xanthoparmelia )". Australian Journal of Chemistry. 32 (11): 2565. doi:10.1071/CH9792565.
  28. "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene" . Retrieved 2007-08-16.
  29. May also be considered to be related to sex.
  30. Nordenström, Björn E. W. (1951). "Effect of cadaverine and lysine on the urinary excretion of piperidine in rabbits". Acta Pharmacologica et Toxicologica. 7 (3): 287–296. doi:10.1111/j.1600-0773.1951.tb02870.x. PMID   14856760.
  31. "NIST Standard Reference Database 69, June 2005 Release: NIST Chemistry WebBook – Pentachloronitrobenzene" . Retrieved 2007-08-16.
  32. R A Klein, G P Hazlewood, P Kemp, and R M Dawson, Biochem J. 1979 December 1; 183(3): 691–700.
  33. Apitz-Castro R, Béguin S, Tablante A, Bartoli F, Holt JC, Hemker HC (1995). "Purification and partial characterization of draculin, the anticoagulant factor present in the saliva of vampire bats (Desmodus rotundus)". Thromb. Haemost. 73 (1): 94–100. doi:10.1055/s-0038-1653731. PMID   7740503. S2CID   25989455.
  34. De Tullio, Mario C. (2012). "Beyond the Antioxidant: The Double Life of Vitamin C". Water Soluble Vitamins. Subcellular Biochemistry. Vol. 56. pp. 49–65. doi:10.1007/978-94-007-2199-9_4. ISBN   978-94-007-2198-2. ISSN   0306-0225. PMID   22116694.
  35. Theerasilp S, Kurihara Y (August 1988). "Complete purification and characterization of the taste-modifying protein, miraculin, from miracle fruit". J. Biol. Chem. 263 (23): 11536–11539. doi: 10.1016/S0021-9258(18)37991-2 . PMID   3403544.
  36. Prelog, V., Seiwerth, R. (1941). "Über eine neue, ergiebigere Darstellung des Adamantans". Berichte. 74 (11): 1769–1772. doi:10.1002/cber.19410741109.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  37. Not to be confused with the fictional material adamantium
  38. Parent Hydride Names and Substantive Nomenclature (PDF). IUPAC. March 2004. p. 16.
  39. Charles O, Coolsaet B (1972). "[Prevention of hemorrhage in prostatic surgery. Apropos of the study of the hemostatic activity in prostatectomy of a new molecule: beta-naphthoquinone monosemicarbazone (Naftazone)]". Annales d'Urologie (in French). 6 (3): 209–212. PMID   4562066.
  40. "PEPPSI Catalysts" . Retrieved 2009-04-01.
  41. Curran, Dennis P. (1985). "Tandem radical approach to linear condensed cyclopentanoids. Total synthesis of (.+-.)-hirsutene". Journal of the American Chemical Society. 107 (5): 1448–1449. doi:10.1021/ja00291a077.
  42. Nozoe, Shigeo (1976). "Isolation, structure and synthesis of hirsutene, a precursor hydrocarbon of coriolin biosynthesis". Tetrahedron Letters. 17 (3): 195–198. doi:10.1016/0040-4039(76)80013-5.
  43. SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
  44. Kouřimský, Jiří (1974). A Colour Guide to Familiar Minerals and Rocks. Translated by Náglová, Zdenka. Octopus Books. p. 94. ISBN   0706404084.
  45. Toma, SH; Uemi, M; Nikolaou, S; Tomazela, DM; Eberlin, MN; Toma, HE (2004). "{trans-1,4-Bis[(4-pyridyl)ethenyl]benzene}(2,2'-bipyridine)ruthenium(II) Complexes and Their Supramolecular Assemblies with β-Cyclodextrin". Inorg Chem. 43 (11): 3521–3527. doi:10.1021/ic0352250. PMID   15154817.
  46. Schleyer, Paul von Rague; Eiji Osawa; Michael G. B. Drew (1968). "Nonacyclo[11.7.1.12,18.03,16.04,13.05,10.06,14.07,11.015,20]docosane, a bastard tetramantane" (PDF). J. Am. Chem. Soc. 90 (18): 5034–5036. doi:10.1021/ja01020a053 . Retrieved 2007-08-15.
  47. Derek, Lowe (2010-02-23). "Things I Won't Work With: Dioxygen Difluoride". In the Pipeline. Retrieved 2019-04-02.
  48. Sam Kean (2011), The Disappearing Spoon, Little, Brown, p. 36, ISBN   9781446437650

Bibliography