Fun_People Archive
29 Mar
Molecules with Silly or Unusual Names

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Subject: Molecules with Silly or Unusual Names

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Molecules with Silly or Unusual Names

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

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

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. If you know of any other
potential candidates for this page, please let me know.

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?)...

© 2000 Peter Langston