Molecules with Silly or Unusual Names

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)

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?)...