www.bris.ac.uk/Depts/Chemistry/MOTM/silly/sillymols.htm
Believe it or not, some chemists do have a sense of humour, and this page is a testament to that. Here we'll show you some real molecules that have unusual, ridiculous or downright silly names.
People from all over the world have sent me so many contributions to this page, that I've now had to split it into three smaller pages. The 3D structure files of many of these molecules can be obtained by clicking on the images.
Arsole Yes, believe it or not, there is actually a molecule called Arsole... It is the arsenic equivalent of pyrrole, and although it is rarely found in its pure form, it is occasionally seen as a sidegroup in the form of organic arsolyls. For more information, see the paper with probably the best title of any scientific paper I've ever come across: "Studies on the Chemistry of the Arsoles", G Markl and H Hauptmann, J Organomet. Contrary to popular belief, however, the arsoles are not aromatic... Furthermore, the structure where arsole is fused to a benzene ring is called 'benzarsole', and apparently when it's fused to 6 benzenes is called 'sexibenzarsole', although that molecule hasn't been synthesised yet.
click for 3D structure Adam Ant Adamantane This molecule always brings a smile to the lips of undergrads when they first hear its name, especially in the UK. For those not in the know, Adam Ant was an English pop star in the early 1980's famous for silly songs and strange make-up. Bastardane This is actually a close relative of adamantane, and its proper name is ethano-bridged noradamantane. However because it had the unusual ethano bridge, and was therefore a variation from the standard types of structure found in the field of hydrocarbon cage rearrangements, it came to be known as bastardane - the "unwanted child". A Nickon and EF Silversmith, 'Organic Chemistry: The Name Game', Pergamon, 1987 .
It is named after the architect Buckminster Fuller who designed the geodesic dome exhibited at Expo '67 in Montreal, from which Sir Harry Kroto got the idea how 60 Carbon atoms could be arranged in a perfectly symmetrical fashion.
Charles Turner for the names of the other fullerenes which came from: 'Fullerenes', by Robert F Curl and Richard E Smalley, Scientific American October 1991. Megaphone Despite having a ridiculous name, the molecule is quite ordinary. It gets its name from being both a constituent of Aniba Megaphylla roots and a ketone.
These are ring structures in which the positive and negative charge are delocalised, and which cannot be represented satisfactorily by any one polar structure. They got their name when Huisgen called them after the city Munich (Mnchen), after similar compounds were called sydnones after Sydney. Thanks to Matthew J Dowd, Virginia Commonwealth University, Richmond, VA, for supplying this one. Unununium I know this is technically an element, not a molecule, but it's got such a ridiculous name I thought I'd include it. This is actually element number 111, and is so new it doesn't have a proper name yet. So until it's named after a dead chemist (or physicist) it rejoices in the IUPAC temporary systematic name of unununium. Let's just hope this element doesn't form ring or cage structures, otherwise we might end up with unununium onions...
Unununium Cummingtonite A sample of pyroxmangite, with white pieces of cummingtonite visible toward the lower left. Cummingtonite This mineral must have the silliest name of them all.
It got its name from the locality where it was first found, Cummington, Massachusetts, USA. Putrescine, Cadaverine, Spermine and Spermidine Putrescine originates in putrefying and rotting flesh, and is quite literally, the smell of death. It is one of the breakdown products of some of the amino-acids found in animals, including humans. Although the molecule is a poisonous solid, as flesh decays the vapour pressure of the putrescine it contains becomes sufficiently large to allow its disgusting odour to be detected. It is usually accompanied by cadaverine (named after the cadavers that give rise to it), a poisonous syrupy liquid with an equally disgusting smell. Putrescine and cadaverine also contribute towards the smells of some living processes. Since they are both poisonous, the body normally excretes them in whatever way is quickest and most convenient. For example, the odour of bad breath and urine are 'enriched' by the presence of these molecules, as is the smell of semen, which also contains the related molecules spermine and spermidine.
Virtual Museum of Minerals and Molecules Moronic Acid This is a triterpenoid organic acid that is found in Pistacia resin, and is therefore of interest to people studying archaeological relics, shipwrecks and the contents of ancient Egyptian jars.
Moronic Acid - click for 3D structure Moronic acid Curious chloride Curious Chloride and Titanic Chloride The trivial name for some curium compounds can be either curous or 'curious', so curium trichloride becomes curious chloride. However the only curious property it has is that it's sufficiently radioactive that a solution, if concentrated enough, will boil spontaneously after a while.
Fukalite - the red marker is 3mm long Traumatic Acid This is a plant hormone which causes injured cells to divide and help repair the trauma - hence its name, and its synonym 'wound hormone'.
Fucitol again Fucitol Although this sounds like what an undergraduate chemist might exclaim when their synthesis goes wrong, it's actually an alcohol, whose other names are L-fuc-ol or 1-deoxy-D-galactitol. It gets its wonderful trivial name from the fact that it is derived from the sugar fucose, which comes from a seaweed found in the North Atlantic called Bladderwrack whose latin name is Fucus vesiculosis. Interestingly, there are a few articles in the Journal of Biochemistry throughout 1997 concerning a kinase enzyme which acts on fucose. The creators of these articles were Japanese, and seemed to have missed the fact that fucose kinase should not be abbreviated as 'fuc-K'.
Dr Stephen O'Hanlon from the Orthopaedics Dept of Bedford Hospital for the information on fucose kinase. Erotic Acid No, this isn't the world's best aphrodisiac. Its correct name is orotic acid, but it has been misspelt so often in the chemical literature that it is also known as erotic acid! Apparently, if you add another carbon to it, it becomes homo-erotic acid...
Bastardin-5 - click for 3D structure file Bastadin-5 This is just one of a number of bastadins, which are molecules isolated from the marine sponge Ianthella basta. They possess antibacterial, cytotoxic and anti-inflammatory properties.
Bastardin-5 - click for 3D structure file Vomicine This poisonous molecule gets its name from the nut Nux Vomica, which is the seed of a tree found on the coasts of the East Indies. The seeds are sometimes called 'Quaker buttons', and are a source of strychnine as well as the emetic vomicine.
Rhamnose - click for 3D structure Has Posh Spice just been given some rhamnose? Gossypol This ridiculously named molecule is found in cotton seeds. It was used as a male contraceptive in China, but was never used in the West (and may have since been banned in China as well), since its effects were permanent in about 20% of patients!
Skatole - click for 3D structure Skatole This molecule's name comes from 'skatalogical', meaning concerning fecal material. Its proper name is 3-methylindole, but it gets its trivial name from the fact that it is a component of feces. Surprisingly, it is also found in coal tar and beetroot , and can be obtained synthetically by mixing egg albumin and KOH. As you might guess, skatole consists of white to brownish scales which are soluble in hot water.
It is also the primary product whenever arsenic ores are smelted, and is used in industry as a glass decolourising agent. Another related mineral with a similar silly name is arsenolamprite, which is a native form of arsenic.
Sexithiophene This is a 'sexi' molecule - which means it has 6 sub-units, in this case of thiophene rings. Because of its conjugated system of double bonds, this organic molecule conducts electricity quite well. As a result, it is one of a number of similar molecul...
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