More 'Found Molecules'

This week, I've rounded up three examples of "molecules" - one real, two not-so-real - from the world outside the lab.

Source: Wellcome trust

Amino Acid - I watched a YouTube clip of Guardian Neurophilosophy blogger Mo Costandi explaining to the Wellcome trust about why he blogs (Fun Fact: Mo worked as a security guard prior to becoming a science writer). At the end of the video, Wellcome displays a splash card with a mission statement and a ball-and-stick model: hey, it's L-serine! It's always nice to see a correctly-drawn molecule in advertising, especially when they could have picked a neuron, a cell, or a goofy staged picture instead (Watch, as science blogger adds droplets to bright red solution!!!).

Of course, my science spider-sense needs to clarify two very minor points. First: at neutral pH, solitary amino acids usually like to exist as zwitterions, which would mean that the nitrogen (blue) picks up a proton, and the carboxylic acid (red) loses one (COO-). Two: since we're discussing neurology here, I can't help but feel that they might have meant to show neurotransmitter D-serine, the enantiomer (mirror image). Turns out, the body generates D-serine from L-serine in the brain using a specific enzyme, serine racemase.

Found: hanging on the Shell station door

Nitrogen Enhanced Gas - Last month, Shell Oil company released a new generation of its detergent-containing gasoline, designed to protect your engine from "performance-robbing gunk," or carbon deposit buildup on intake valves. Look at their new logo*, pasted all over the station's pumps, doors, and road signs: what the heck is that blue thing? Counting quickly, I'd assume that it's nonane, the 9-carbon cousin of octane, the main component of gasoline. Well, that can't be it, because that doesn't have any nitrogen! Writer Michael McCoy came up against the same such pseudo-scientific "ziggy-zaggy molecule"  in his C&EN article (Chem. Eng. News 2009, 87(14), 20-21).

Digging briefly through the patent lit, I came across US7,901,470B2 (2011), titled simply "Gasoline Additives," and co-written by six Shell Oil engineers. A sampling:

"a hydrocarbyl amine...in the range 155 to 255 as an additive in unleaded gasoline...for reducing injector nozzle fouling..." 

Looks like we're on the right track. Read a few more 'grafs down, and they mention...dodecylamine. In fact, they say "...found to be particularly effective," which in patent-speak means they should probably add a few more carbons and an amine group onto that sign! On a more serious note, there's a debate brewing over whether such detergents help engines while harming the atmosphere, by producing extra NOx emissions.

Credit:  ST:TNG | Paramount Pictures

Star Trek Set Design - Watching through old episodes of ST:TNG, a tiny detail caught my eye. In the 24th Century, young Wesley Crusher, the oft-misunderstood teen wunderkind, studies such subjects as nano-engineering, quantum physics, and...chemistry? Check out this screen shot from season 3, episode 1; it seems researchers in Stardate 43125.8 are still using the old HGS modeling kit (a personal favorite, btw).

And what structure do we have here? Judging by the color-code, normally, red = O, black = C, white = H, I'd guess a type of dual hyperoxygen**, an oxygen with four connected bonds (oxygen usually likes two bonds, or 3, tops). I've heard of Olah's hypercarbon, so maybe it's a take on that? Perhaps a form of matter we just haven't found yet? More likely, following the example from National Lampoon's Christmas Vacation, set designers simply aren't versed in synthesis.

Dear Hollywood - If you need to vet a structure or formula, do feel free to ask me. Operators with chalkboards and books are standing by!



*Editor's Note: Is that a registered trademark (R) symbol next to the word "nitrogen?" I wasn't aware that element names could be trademarked! Of course, I'll be immediately contacting the Just Like Cooking legal department to file for Argon(TM), Strontium(TM), Niobium(TM), and Roentgenium(TM). Y'all can fight over the rest.
**Bonus Round: Try putting "hyperoxygen" into Google. Mostly homeopathic cures, hyperbaric chambers, and folks who don't know what hydrogen peroxide really is.

In Praise of Portmanteaux

Listening to the news on the drive home, some interesting words crossed my ears: Fracking. Locavore. Flexitarian. 


It's clear that we generate neologisms nowadays simply by stitching old words together.

I'm tired of writing this sinfo on microsyn...time for skitter?

The trend has a name: portmanteau words. Attributed to wordsmith Lewis Carroll in the late 19^th Century, the practice has evolved with the internet age to describe complex ideas in tiny verbal bundles. For instance, a locavore is a "local omnivore," or someone who eats foods located sourced from within a certain radius of his home. 


Not that we chemists should be surprised. After all, we're responsible for many of these words, and we use them every day. The aldol reaction takes an aldehyde and an enol to forge new carbon-carbon bonds. Using small organic molecules for catalysis? Organocatalysis. Why talk about reduction and oxidation cycles, when you could just say redox?


So, in an effort to increase synthetic chemists' efficiency, I'd like to propose several new portmanteau words:


sinfo: Supplementary Information
chactalysis: C-H Activation Catalysis
fuells: Fuel cells
meconomy: The "Methanol Economy"
Wots: Western blots
flolumn: Flash-column chromatography
microsyn: Microwave-assisted synthesis
skitter: Scientific Twitter  (Does that make Just Like Cooking a 'sklog?')


We could take this trend to a logical extreme, and repurpose words we already have. For instance, what do you call going back through your lab notebooks for an old prep?      
Retro-synthesis!


Commenters - Feel free to chime in....what have I missed?