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.
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.
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.
Fenestranes A class of compounds with a "window pane motif" (the name fenestrane derives from the Latin word fenestra, meaning window), comprising four fusedcarbocycles 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.
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]
(Al2Si2O5(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]
Arsole (C4H5As), an analogue of pyrrole in which an arsenicatom 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]
Constipatic acid [2-(14-hydroxypentadecyl)-4-methyl-5-oxo-2,5-dihydrofuran-3-carboxylic acid], an aliphaticacid derived from the Australian Xanthoparmelialichen.[3][27]
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]
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.
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.
Some Australian lichens, like Parmelia constipata, have this as a component. Protoconstipatic acid, dehydroconstipatic acid, and methyl constipatate are all constipatic acid derivatives.
DiNOsar
Common 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
Gardenin
Gardenins, which are flavones extracted from the Indian plant Gardenia lucida, come in a variety of forms.
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]
Periodic acid Or per-iodic acid, is pronounced /ˌpɜːraɪˈɒdɪk/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.
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.
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]
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.
Dioxygen difluoride, O2F2, an extremely unstable compound which reacts explosively with most other substances – the nickname "FOOF" is a play on its formula.[47]
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.
^"Elusive bowtie pinned down - synthesis of spiropentadiene, a carbonaceous compound nicknamed bowtiediene because it is shaped like a bowtie". Science News. July 13, 1991.
^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.
^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.
^Uri J, Csoban G, Viragh E., Acta Physiol Hung. 1951;2(2):223-8.
^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. S2CID23948075.
^"BARF". ChemSpider. Royal Society of Chemistry. 2013. Retrieved 4 November 2013.
^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.
^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. PMID14856760.
^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. PMID4562066.
^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.
^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.
^SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan, J. Org. Chem., 43(4) (1978) 586
^Kouřimský, Jiří (1974). A Colour Guide to Familiar Minerals and Rocks. Translated by Náglová, Zdenka. Octopus Books. p. 94. ISBN0706404084.
^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. PMID15154817.
Alex Nickon and Ernest F. Silversmith, "Organic Chemistry, the Name Game: Modern Coined Terms and Their Origins", Pergamon 1987. ISBN0-08-034481-X.
Randall, David (February 1, 2004). "Storyville: Molecular scientists have a word for it". The Independent on Sunday. London, England.(subscription required)
Wallechinsky, David; Wallace, Amy (2005). "24. Molecules and amoebas with funny names". The new book of lists : the original compendium of curious information. New York, N.Y.: Canongate. pp. 203–205. ISBN9781841957197.
![[1.1.1]Propellane](/wiki/File:1.1.1-propellane.svg)
