10 Comic Chemicals, presented by Chemistry Cat

This week is National Chemistry Week in the US, so I thought I’d take this opportunity to showcase some of the more unusual chemicals. To make it interesting, we also have Chemistry Cat giving his/her (?) thoughts on the comic compounds.

1. C4H4AsH
Any guesses as to the common name of this chemical? ArsoleYup, that is Arsole.

The chemists have really gone to town on this one, writing papers such as Studies on the Chemistry of the Arsolesand sticking six of them together to get a ‘sexiarsole‘. One study looks at whether arsoles smell. Due to the wonders of the academic publishing system, access to these fascinating insights will cost you $65. Other contributions to this expanding niche include Unusual Substitution in an Arsole Ring and Arsole metal complexes.

Arsole Meme

2. C20H30O4
3. C33H40O1
Vaginatin
and Clitorin 1. The name Vaginatin comes from Selinum vaginatum, the plant from which the chemical was extracted. It contains lots of oil and is used in Indian herbal medicine.

Vaginatinclitorin   4. Mg2Mg5Si8O22(OH)2 CummingtoniteA long time favourite of geologists, chemists, and other sciency types, that little lump of rock there is called Cummingtonite. It got its name from the locality where it was first found, Cummington, Massachusetts.

cat-cummingtonite

5. Apolloane
6. Rocketene
Apolloane was synthesised around the time of the Apollo 11 moon landings, and when drawn looks like a rocket. The OH is located at carbon 11, making the full name apolloane-11-ol. Legend has it that Neil Armstrong’s has a copy of the paper which named it. 2

cat-apolloane

7. Arsenical Diphenylaminechlorarsine
Adamsite is an organic compound used in riot control and chemical warfare. It was independently developed one Roger Adams in 1918. Within minutes of inhaling even the smallest amount, you will be vomiting and sneezing all over the place. Good work, Mr. Adams. It was used by the US in the Vietnam war, and is now being produced and stockpiled by North Korea.

cat-adamsite

8. Ca4Si2O6(CO3)(OH,F) 2
Fukalite
 gets its name from the Fuka mine in the Fuka region of southern Japan. It is very rare, and is a form of calcium silico-carbonate.

fukalite

8. Ca2SbMg4FeBe2Si4O20
Welshite is named after the American amateur mineralogist Wilfred R. Welsh.

9. Diethyl azodicarboxylate
This chemical is abbreviated to DEADCAT. It is toxic, shock and light sensitive, and can violently explode when heated above 100°C.

cat-deadcat

10. 3,4,4,5-tetramethylcyclohexa-2,5-dien-1-one/C10H14O
Also known as Penguinone and probably the cutest molecule ever!

1. Penguin. 2. Penguinone.

1. Penguin. 2. Penguinone.

For more penguin-themed goodness in academia, see this previous post.

 

Bonus: The final two are more chemistry thought experiments, but they are pretty cool nonetheless.

11. Chemistry: the human dimension
The Nano Putian group of chemicals are proposed in a paper called Synthesis of Anthropomorphic Molecules. Standing at a diminutive 2-nm-tall, these tiny figures have nonetheless drawn 13 citations!

The Nano Putians   The Nano Putians

 

12. Old MacDonald (had a meth lab)
Ever wondered what your childhood songs would have been like if the characters pursued alternative career paths? Well now you can get a sense of what would happen if Old MacDonald left his farm to become a professor of organic chemistry. The paper Old MacDonald Named a Compound: Branched Enynenynols, proposes some whimsical compounds as a method to teach students chemistry nomenclature rules.

Old MacDonald

Many thanks to Paul May for his incredibly comprehensive page and book on funny molecules which inspired this post.

  1. The closest that male chemists get to female anatomy?
  2. Neil has unfortunately not returned my request for comment.

I’ll Put the Kettle On: the academic’s guide to making the perfect cuppa

This is a slightly edited version of a post that originally appeared on the Guardian Higher Education blog.

As a British researcher working in France, I have struggled with an existential crisis regarding my choice of hot beverage. I have always been a tea drinker, yet the social pressure to drink coffee here is almost as overpowering as the coffee itself. My boss thinks I only drink tea to impress female colleagues, though combined with a big red beard and the French language skills of a three year old, it probably only serves to further mark me out as the office oddball.

To make matters worse, there is no communal milk, only an endless supply of olive oil, salt, and balsamic vinegar.

Not a drop of milk in sight.

Not a drop of milk in sight.

Nonetheless, I patriotically persist, following the sage advice of the UK Ministry of Munitions (1916) that “an opportunity for tea is regarded as beneficial both to health and output”.

Fellow Guardian blogger, Dean Burnett, recently discussed the science on brewing the perfect cuppa, arguing that the premise of this age-old question is itself so subjective that it can never be definitely answered. Personally, I always start out with loose-leaf Assam, filtered water, milk and white sugar, as per the Royal Society of Chemistry guidelines. And I NEVER reboil the water, perish the thought. But though the science of brewing tea has been done to death, there is an emerging field of scientific inquiry regarding best post-brew practice.

For example, sometimes I really go for it and crack out the teapot. Unfortunately, when it comes to pouring I always get that pesky dribble down the underside of the spout (the ‘teapot effect’); it drives me mad (‘first world problems’). This effect has been helpfully modelled in a Physics of Fluids paper, while a further paper, ironically written by four Frenchmen, identified a number of factors that affect dribbling. These include: “curvature of teapot lip; speed of flow; and ‘wettability’ of teapot material”. The main culprit, the ‘hydro-capillary’ effect, can easily be overcome by either thinning the spout, or by applying superhydrophobic materials to the lip.

Beating the ‘teapot effect’ with a superhydrophobic coating

Beating the ‘teapot effect’ with a superhydrophobic coating

Then comes the stirring. Or at least it would if I could ever find a teaspoon. I had often lamented the lack of information on the “displacement of teaspoons in institutional settings” in the scientific literature. Fortunately, some Aussie researchers (presumably with nothing better to do) launched a ‘longitudinal cohort study’ to figure out “Where have all the bloody teaspoons gone?” They meticulously tracked 70 teaspoons for 5 months, observing a staggering loss of 80% and a teaspoon half-life of 81 days. The researchers were, however, stumped as to why this occurs, with “escape to a spoonoid planet” being one plausible explanation.

Spoon loss

Finally, the fraught walk back to the desk, and the inevitable hand scalding as a third of the tea I just lovingly brewed sloshes onto the floor. Indeed, A paper in Physical Review E is sympathetic: “in our busy lives, almost all of us have to walk with a cup… often we spill the drink”. Researchers conducted an experimental study on beverage spillage, controlling for various walking speeds and initial liquid levels. Thankfully, I now know all the best techniques for staying within the ‘critical spill radius’ (i.e. the edge of the mug).

Motion of the liquid within the ‘critical spill radius’

Motion of the liquid within the ‘critical spill radius’

Tea isn’t really tea unless you get the biscuits involved, and academics have even overthought this simple pleasure. ‘Washburn’s Equation’ describes how liquid moves through the biscuit, while a team of mechanical engineers used a gold-plated digestive to figure out how best to dunk. You need a full cup and an angled entry, but the real trick is to flip the biscuit post-dunk so that the drier side supports the weaker side as you move from mug to mouth.

Washburn’s Equation

Washburn’s Equation

 

The Best Thing I’ve Seen This Week

Academics tweeting faux campus society announcements (#UniSocieties). My favourites include: The Statistics Society (“Stats Soc has taken delivery of large consignment of tea. There will be a student T-distribution next week.”); The Short Attention Span Society (“Will meet on… oops, I stepped in… are they serving burritos for… I forgot my…”); and The Societies Society (“promoting meta-analysis and academic overthinking”). I took this opportunity to highlight that that LSE Rugby Club will not meet at all this year, having been disbanded for their misogyny and homophobia.

Overheard on Twitter

So there you have it, the perfect cuppa from brew to biscuit, with a bit of academic humour on the side. Just don’t forget to do the washing up. Oh, and please do tweet me @AcademiaObscura if you have any spare superhydrophobic materials lying around.

Penguins

Penguins are adorable. On this we can all agree. Perhaps it is through their sheer cuteness that they have managed to waddle their way into some rather obscure corners of academia. Here we give you our favourite Penguin papers and other tidbits. Please do let us know if you find Penguins turning up elsewhere.

A 'Penguin' diagram, before the infusion of darts, beer, and drugs.

A ‘Penguin’ diagram, before the infusion of darts, beer, and drugs.

1. Particle Physics Penguins
Perhaps the most famous use of the Penguins likeness comes from particle physics, where it is used to represent “[something very complicated in high energy physics that I don’t understand at all]”.

What is perhaps less well-known is how these diagrams came about. Originally, the Penguin diagrams looked nothing like Penguins. That all changed when John Ellis, now Professor of Theoretical Physics at King’s College London, went for a drink with Melissa Franklin and Serge Rudaz. As he recalls:1

In case you were struggling to see the resemblance...

In case you were struggling to see the resemblance…

Melissa and I started a game of darts. We made a bet that if I lost I had to put the word penguin into my next paper. She actually left the darts game before the end, and was replaced by Serge, who beat me. Nevertheless, I felt obligated to carry out the conditions of the bet.

It is worth noting that this loss was in itself rather improbable. Rudaz later admitted that for him to beat Ellis at a game of darts was a “miraculous event”: “John was a very strong player and had his own set of darts which he brought to the pub”.2 Nonetheless, Ellis now had to find some way to work Penguins into his next paper, no easy task.

For some time, it was not clear to me how to get the word into this b quark paper that we were writing at the time. Then, one evening, after working at CERN, I stopped on my way back to my apartment to visit some friends living in Meyrin where I smoked some illegal substance. Later, when I got back to my apartment and continued working on our paper, I had a sudden flash that the famous diagrams look like penguins. So we put the name into our paper, and the rest, as they say, is history.

penguin_chalk

John Ellis drawing up one of his famous physics Penguins.

Of course, the scientists were not happy with just one type of Penguin, so a new Super Penguin was subsequently spawned.3

This is just, brilliant.

This is just, brilliant.

2. Chemistry Penguins
Not to be outdone by the physicists, the chemists decided to get in on the joke. Said chemists decided that 3,4,4,5-tetramethylcyclohexa-2,5-dien-1-one was rather a dull name for a chemical. Noting that its skeletal formula looked quite like a Penguin, they decided to give it the common name Penguinone.4

1. Penguin. 2. Penguinone.

1. Penguin. 2. Penguinone.

penguin33. Penguin Poo
You may or may not be aware that Penguins, in particular Chinstrap and Adelie Penguins, defecate rather forcefully. This fact evidently proved worthy of further study to Dr. Victor Benno Meyer-Rochow and Jozsef Gal, who published a dedicated paper in Polar Biology: ‘Pressures produced when penguins pooh—calculations on avian defaecation‘. Dr. Meyer-Rochow describes how this unusual paper came to be:5

Our project started in Antarctica during the first (and only) Jamaican Antarctic Expedition in 1993… Many photographs of penguins and their “decorated” nests were taken. Later at a slide show… I was asked by a student during question time to explain how the penguins decorated their nests. I answered: They get up, move to the edge of the nest, turn around, bend over- and shoot… she blushed, the audience chuckled, and we got the idea to calculate the pressures produces when penguins poo.

penguin_poop

A helpful diagram.

As with many of the more unusual papers that we have found lurking in the backwaters of academia, Penguin Poo elicited a number of genuine scientific research questions.6 A palaeontologist studying dinosaur biology thought that the calculations could be applied to similar streaks found near fossil dinosaur nests, zoo-operators inquired about ‘safe’ distances for visitors, and a medical researcher was inspired to recalculate the same measures for humans, as that data was now quite old!7

Penguin poo, as it turns out, can serve another useful purpose: locating Penguin colonies from space. In a paper entitled ‘Penguins from space: faecal stains reveal the location of emperor penguin colonies‘, researchers used satellite imagery to spot distinctive brown stains on the ice, left by Emperor Penguin colonies. Using this technique, they were able to locate 10 new colony locations, reposition six known locations by over 10 km, and rule out 6 old locations.

If you are not already tired of Penguins, there is of course a huge body of research concerning these beautiful birds that can keep you amused for hours. Recent finds include decoding of a ‘language’ used by Jackass Penguins and discovery of fossils of a giant, 2m tall, Penguin. Or you can just leave it here, happy in the knowledge that Norway once knighted a Penguin :-).

Nils Olav receiving his knighthood.

Nils Olav receiving his knighthood.

  1. Ellis passed on his recollections to Mikhail Shifman, who subsequently reproduced them in the foreword to his book, ITEP Lectures in Particle Physicshttp://arxiv.org/pdf/hep-ph/9510397v1.pdf
  2. Vainshtein, A., ‘How Penguins Started to Fly’ (Sakurai Prize Lecture, 1999) http://arxiv.org/pdf/hep-ph/9906263.pdf.
  3. Dujmic, D., ‘BaBar Searches for Super-Penguins’ (September 14, 2006) SLAC Today http://today.slac.stanford.edu/a/2006/09-14.htm.
  4. The lovely people over at i can has science did a bit of digging and found that Penguinone is mentioned in the literature around 10 times, but that searches of a chemistry database produced no results. It is therefore not clear whether a chemist actually named this molecule, or whether the internet has worked its magic and nobody has the heart to dispel the myth.
  5. Personal website: http://www.meyer-rochow.com/penguinpoo.htm
  6. Personal website: http://www.meyer-rochow.com/penguinqa.htm
  7. It is not immediately clear exactly what the practical application of such measurements is.

The Last Writes: posthumous publishing

Over on his Chemical connections blog, Stuart Cantrill posted an article last year entitled ‘The Last Writes‘.1  He mentions a number of academics, chemists in particular, that have published posthumously. In the arts and in literature it is not at all uncommon for works to be released after death, however it is hard to imagine many cases where the same might apply in academia. Perhaps there is a 3-4 year window left open by the glacial pace of academic publishing, but beyond that, your days are numbered, so to speak. Two instances in particular caught my eye.

Firstly, Alfred Werner, the first inorganic chemist to win the Nobel prize. A paper published in 2011 used the ubiquitous asterisk footnote to flag the fact that one author, Werner, died in 1919. This means that Werner published his most recent paper a staggering 82 years after his death!

Coming a distant second in this rather bizarre contest is another Nobel laureate in Chemistry, Robert B. Woodward. Woodward was the preeminent chemist of his day, and was known for synthesising many natural compounds for the first time. Woodward authored around 200 papers in his life and was so prolific in the lab that the pace of his scientific discoveries outstripped his ability to publish. As a result, much of his work was published after his death. So it was that in 1993 Woodward was able to co-author a paper, 13 years after his death.

I haven’t been able to find any examples of posthumous publishing in other fields. If you come across any, please do let me know!

  1. Thanks Stuart for the great pun. Try as I might, I couldn’t better this one!