Molecules with Silly or Unusual Names

  1. Molecules with Silly or Unusual Names

    >From Paul May's website at Bristol University:
    http://www.bris.ac.uk/Depts/Chemistr.../sillymols.htm

    (This was featured in New Scientist magazine, Jan 17th 2000)


    Arsole
    Yes, believe it or not, there is actually a molecule called Arsole... and
    it's a ring! 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.Chem.,
    248 (1983) 269. Contrary to popular belief, however, the arsoles are not
    aromatic...

    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 E.F. Silversmith, 'Organic Chemistry: The Name Game',
    Pergamon, 1987].

    Buckminster Fullerene
    This is the famous soccerball-shaped molecule that won its discoverers the
    Nobel prize for Chemistry in 1996. 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. Because the name of the
    molecule is a bit of a mouthful, it is often referred to just as a Bucky
    Ball.

    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.
    [S.M. Kupchan et al, 'J.Org.Chem.', 43 (1987) 586].

    Munchnones
    No, these aren't the favourite compound of the Munchkins from The Wizard of
    Oz, but are in fact a type of mesoionic compound. 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 (Munchen), after similar
    compounds were called sydnones after Sydney.
    Huisgen et al. Chem. Ber. 1970, 103, 2611.
    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...
    [See Pure and Appl. Chem. 51 (1979) 381 for the naming scheme].

    Cummingtonite
    This mineral must have the silliest name of them all. Its official name is
    magnesium iron silicate hydroxide, and it has the formula
    (Mg,Fe)7Si18O22(OH)2. It got its name from the locality where it was first
    found, Cummington, Massachusetts, USA.

    Putrescine and Cadaverine
    Putrescine originates in putrefying and rotting flesh, and is quite
    literally, the smell of death. It contains two amine groups, one at either
    end of the molecule, and 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 usuallyaccompanied 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 smell
    of semen and urine are 'enriched' by the presence of these molecules, as is
    the odour of bad breath.

    Dickite
    Dickite, Al2Si2O5(OH)4, is a (kaolin) clay-like mineral which exhibits
    mica-like layers with silicate sheets of 6-membered rings bonded to
    aluminium oxide/hydroxide layers. Dickite is used in ceramics, as paint
    filler, rubber, plastics and glossy paper. It got its name from the
    geologist that discovered it around the 1890s, Dr. W. Thomas Dick, of
    Lanarkshire, Scotland.

    Moronic Acid
    This is a triterpenoid organic acid that is found in Pistacia resin, and is
    therefore of interest to people studying archaelogical relics, shipwrecks
    and the contents of ancient Egyptian jars. But why it's called moronic acid
    is still unknown... Derivatives of this are called moronates.
    Ref: P.L. Majumdar, R.N. Maity, S.K. Panda, D. Mal, M.S. Raju and E.
    Wenkert, J.Org.Chem. (1979) 44, 2811.
    Thanks to Dr Ben Stern of Bradford University for supplying this one.

    Curious Chloride and Titanic Chloride
    The trivial name for some curium compounds is '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. In a similar way, titanium
    compounds can be 'titanic', so we get the wonderfully named titanic
    chloride, TiCl4. It's also interesting to know that in the titanium
    industry, TiCl4 is known as 'tickle'.
    Thanks to Beveridge and Dr Justin E. Rigden for supplying these two.

    Traumatic Acid
    This is an organic acid with two carboxylic acid groups, one at each end. I
    don't know where the name came from, or much about it...anyone know?
    Thanks to Dr Neil Edwards of Sussex University for supplying this one.

    Arabitol
    No, this has nothing to do with rabbits - it's an organic alcohol that's one
    constituent of wine. It's also known as pentahydric alcohol.
    Thanks to David Brady for supplying this one.

    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.
    Thanks to David Brady for supplying this one.

    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! Another name for it is vitamin B13.
    Apparently, if you add another carbon to it, it becomes homo-erotic acid...
    Thanks to Gerard J. Kleywegt of Uppsala University for info on this
    molecule.

    Pending...

    There are some molecules that I've heard of but don't have information about
    or I don't know the structure. I'm not even sure if they are genuine
    molecules. If you can help with any of these, please let me know. They are:
    Penguinone, Windowpane, Homo-Erotic acid (is the above info about this
    molecule true?)...
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Molecules with Silly or Unusual Names