Friday Fun: WWWTP? Linkin Park Edition

Through the wonders of the Internet, I've found this still image from the 2003 Linkin Park video for "Numb":

In the video, a young, disaffected student dreams of traveling to far-flung cities to practice her true talent - sculptural drawing. However, it seems an evil chemistry professor stands in her way.

But look behind the (hilariously stereotyped) man with the chalkboard pointer. NaK...as an alloy, perhaps? And how come there's a subscript number before the nitrous acid?

If that were my science teacher, I'd feel "numbed" by his complete lack of chemistry education.

Happy Friday,
See Arr Oh

A Nudge Towards "Scrudge"

Last night, while I trudged through Alexander Shulgin's seminal work* PiHKAL, I came upon scrudge, a fantastic heretofore-unknown-to-me term for a very common phenomenon:

Love this word: "Scrudge." Defined in the #PiHKAL appendix, meaning low-running TLC impurities that may hamper rxn monitoring.
— See Arr Oh (@SeeArrOh) January 27, 2015

Here's the reaction Shulgin attempted:

And, in his own words (emphasis mine):

"The elephant labored and brought forth a mouse. A lot of work for a material without activity. 

I have used the term "scrudge" in this and other recipes, without defining it. With this aldehyde, as with most aldehydes where there is no ortho substituent on the benzaldehyde, the reaction progress should be carefully followed by thin-layer chromatography. As the aldehyde disappears from the reaction mixture, the nitrostyrene appears, but there is usually the development of one or more slower-moving components as seen by TLC. Such a wrong-product is called scrudge."

Scrudge just works. Not to judge, but any synthetic drudge could tell you they've experienced the same. On scrudge, I won't budge. Just look at the beautiful art inspired by just such a smudge:

Credit: Vittorio, who blogs over at Labsolutely

This post's a bit of a kludge, but I hope I've provided a nudge towards scrudge.
Feel free to use it in your next lab meeting or thesis defense!

--

*"Phenethylamines I Have Known and Loved"

Science Blackout Poetry, Round 2

Round 1

JACS 2006, 10596

(These are really fun to do!)

R.B. Woodward's thesis

Chem. Comm. 1976, 734

Science Blackout Poetry

Inspired by Austin Kleon and the New York Times, honoring National Poetry Month.

Update (April 27): A Reddit commenter (rightly) points out to also assign credit to Tom Phillips' Humument Project...good call!

JACS 2012, 11992

JACS 2014, 5257

JACS 1993, 9293

Golden Bacteria?

An amazing breakthrough (!) recently made the rounds on Wired and Gizmodo: a synthetic chemistry / art-house installation in which microbes "...turn liquid gold into 24-karat gold." Two professors from Michigan State University - a microbiologist and a science artist - teamed up to produce the exhibit, entitled "The Great Work of the Metal Lover," which is currently on display at an Austrian art competition.

Credit: G.L. Kohuth | MSU

Hold your applause - the science doesn't travel well across multiple media outlets. The bacterium in question, Cupriavidus metallidurans, reduces gold(III) chloride solution (likely HAuCl4) and precipitates out pure metallic gold. C. metallidurans actually does have some 'super powers' - the last decade (PubMed) shows similar successes with copper, mercury, and lead. Heck, it's even been shot into space! 

But the MSU press release may win the hyperbole 'gold medal.' Here's a few choice lines:

"Cupriavidus metallidurans can grow on massive concentrations of gold chloride – or liquid gold, a toxic chemical compound found in nature"

Gold chloride, liquid gold? Oh, you mean the solid gold salt? With almost no tox data on the MSDS?  

"[the installation] uses a combination of biotechnology, art and alchemy to turn liquid gold into 24-karat gold"

Ye Gods. No alchemy here! I'm not a biochemist - just a #KnuckleDraggingOrganiker - but I'd guess there's a perfectly reasonable, well-studied reduction mechanism operating. Can I get a reductase over here? (P.S. the only "liquid gold" I know of is molten gold)

“This is neo-alchemy. Every part, every detail of the project is a cross between modern microbiology and alchemy"

No comment (see above). 

"...the researchers’ success in creating gold raises questions about greed, economy and environmental impact, focusing on the ethics related to science and the engineering of nature"

Unless we're talking phlogiston and aether here, there's no "creation" of gold: it's a reduction. And utilizing a bacterium to do what it likes to do anyway hardly sets up an ethical or social inquiry.

"[this work]...speaks directly to the scientific preoccupation while trying to shape and bend biology to our will within the postbiological age"  

I really don't understand what they're trying to say here. (Perhaps I need to read Art for Dummies...)

OK, scientific criticism aside, the work looks pretty neat. How often do you get to see electrochemistry in an art exhibit? In the end, I guess the ends justify the means - if just a few people look at it, and think "I wonder how that works?" it will have served its purpose.

Art Antics

In case you hadn't heard, B.R.S.M. is running a pictorial carnival of sorts. His angle? To celebrate the upcoming 66th birthday of venerable chemist - and serial "chemical artist" - K.C. Nicolaou. In keeping with the spirit of the game, we were asked to limit our artistic efforts to the same five molecules. Shown below are my (admittedly ridiculous) entries. 

Vancomycin: Profiles, Pathways, and Space Monsters
(with apologies to Jeff Seeman)

Really, it's what I'd always expected to see published...
(The mustache substitutes for the bridging isopropylidene!)

Friday Fun - Lab Arts-n-Crafts

The Leaning Tower of Septa

It's been a long few weeks at the "real job," and I haven't had a lot of time for serious, analytical posts. I'll try to have a few up before month's end. 


Until then, here's a few pics from around the lab. Call it recycling, call it art, call it something to make you smile. It certainly helps me when I'm going past Hour 60 and starting to get punchy...

Watch the thorns on this bouquet...

I've Got the World on a Flask

Abstract Coloring Book: Take Two

The "colored abstract bug" spreads quickly. Since I began cataloguing appearances, they've cropped up in several other journals, including at least 3 examples in just the last 48 hours.


First, here's some ACIEE oroidin fun, courtesy of the Romo and Molinski groups (sea sponge in the background?):

Next, a sweet little palladacycle OM, thanks to the Gonzalez-Herrero and Vicente groups, in Spain (bright yellow, for Pd?):

Finally, submitted for your consideration, this chalcogen cluster assembly graphic from the Holm lab at Harvard, which recently graced JACS ('M' is tungsten, in case you missed it...):

Again, I'd like to point out that I'm not opposed to deft use of color, to draw the eye, differentiate, or point out an otherwise missed detail. But when the abstracts look more like abstract art? Too much.


Side Note: I couldn't resist showing one more, even though it's not from this past week. A 2011 KCN classic, nonetheless - behold, Epicoccin G (now in color!)

Found Chemistry - Landmark Gate with Chemical Message

On a recent visit to a major US university, I had occasion to stop outside the towering steel gates leading into the main courtyard of the newly-constructed chemistry building. I glanced up, and saw organic molecules, decked out in bronze, blue, and red.

On either side of the gate are polypeptides, four residues each, that use standard amino acid abbreviations to spell out a four-letter word* on either side. Pictured (at left) is the left-hand gate. 


Here are artistic molecules done right - correct bond angles, color-coded atoms, even double bonds! They're certainly better rendered than most of the recent ChemBark "WWWTP?" posts.


*(Need a hint? Only so many schools have four-letter names!)