Move On Along to Colorblind Chemistry for more Bumper Cars!

This is just to say

I have allowed
Dr. Marshall
to take over
this column

and which
you were probably
clicking
for updates

Forgive me
they needed a home
he has time
I have less

With apologies and kudos to both William Carlos Williams and Chemjobber, who enjoys adapting it from time to time.

A Tale by Mail

Long-time readers will no doubt be aware of my running affectation with the "Profiles, Pathways, and Dreams" series of books from ACS; books which, had I not read them in grad school, would probably cause this blog to never exist.

So I have a sneaky hobby: scouring the Internet's used book counter to assemble an entire set. Thus far, I've collected 17 of the 22 from the original 1990-1995 run. As I'm simultaneously trying for thrift, I'm proud to say the most I've paid for one of these books was around $25.

One of the best came in the mail only today - a first-edition, basically mint copy of Djerassi's Steroids Made it Possible. You know, the one with the picture of Nobelist R.B. Woodward going Mike Tyson's Punch-Out! on another esteemed chemist?

Steroids Made it Possible, ACS Books, p. 60

I open the plastic packaging, breathe in the old-book-paper smell.  But wait, there's no library markings. And the book is, what, 26 years old, and is basically undamaged? Curiously, I opened the cover, and realized that Djerassi himself had dedicated it:

To whom, exactly? Why, to Larry Lehmkuhl, the previous president of St. Jude Medical, according to Bloomberg. And is that really Carl's signature? I've compared it against two *for sale* on eBay and at Amazon - $89 euro and $39.85, as of this writing, respectively - it's the real McCoy.

This, of course, raises more questions: Did Lehmkuhl ever read his gift? Was he from a chemistry background? (I can't find much about him through the usual channels).

Did Djerassi mail out copies of his books, en masse, to anyone interested? If so, perhaps other signed treasures are out there, waiting to be found.

Synthetic Endgame

Inspired by this paper from Melanie Sanford's rocking organometallic group at Michigan.

--

*Pun contest! I could also have called this post...

Gotta Make 'Em All

Poke-Ball and Stick Models

Chantix Charmander

Putting the Fun in C-H FUNctionalization

'All Thumbs' Synthesis

Tough-to-Swallow Propargylation

As I thumbed through the recent Tet Lett abstracts, I encountered this title:

"Regioselective propargylation of aldehydes using potassium allenyltrifluoroborate promoted by tonsil"

Turns out, the authors were referring to Tonsil (R), an acid-treated calcium bentonite clay, not the fleshy pockets in the back of the throat associated with immune response. I guess BRSM  doesn't have to update his "Desperate Conditions" list quite yet...

So, in summary:

This.

Source: Sud-Chemie

Not This.

Friday Fun - Chemical Electronica, CENOnion, Cantrilling

It would surprise no one reading this blog that I'm equally passionate about chemistry and music (see here, here, or here). Thus, I couldn't help but relay this wonderful passage from WIRED about the LinnStrument - a new electronic grid instrument - and its chief enthusiast (highlighting mine):

"By professional standards, Rosengarten is a hack. He’s never had a music lesson in his life. He’s no prodigy either. He’s a 48-year-old chemistry teacher in upstate New York. He can’t read sheet music, and he doesn’t aspire to. Like many people, though, he has a fascination with any new technology that allows him to compose and play songs for fun. In a recent YouTube video, Rosengarten unboxes his LinnStrument and immediately coaxes a decent melody out of it. Like any good teacher, his enthusiasm is genuine and infectious."

Not feeling the good vibrations from this one? Try another of my attempts at humor from C&EN Onion.

Spotted this at a contemporary art museum. Apparently, "cantrilling" has gone mainstream!

Happy Friday,
See Arr Oh 

Fast(er) Track Peer Review

(New York, NY) - BREAKING: Following the recent announcement of a fast-track peer-review option at Scientific Reports, competing journals are pleased to announce their own revolution.

For just $749, authors can now opt-in to ReviewWare's RPS [rock–paper–scissors] peer-review track, which decides each scientific manuscript's fate by a single game of rock–paper–scissors* between the Corresponding Author and a qualified External Referee.

Source: Science Daily

Games Reviews will be conducted over Skype with an editor / adjudicator. To maintain anonymity, the external reviewer will be required to wear a glove. To accommodate increasing requests for double-blind peer review, the author selected to take part in the rock–paper–scissors duel can also choose to be gloved, thus masking his or her "identity."

Should the peer-review process result in the authors' Paper being shredded by the reviewer's Scissors (or their Rock wrapped in Paper, or their Scissors blunted by Rock), then a small additional fee allows authors to select our enhanced "Best-of-Three!" peer-review option.

Following this rigorous new review process does not obviate successfully-reviewed authors from paying standard journal processing fees. No one's that lucky.

--

*For an additional $100, authors can choose the more interactive "Bear Ninja Cowboy" package. Costumes cost extra.

Confused? Check the date.

Friday Fun - Jobs from the Future

Who wants to help me construct a job description for the brave new world of automated synthesis?
Leave your suggestion in the comments, and I'll modify our advert as needed...

March 13, 2025 - Automated Synthesis Engineer

Our company seeks a motivated individual to work in our growing Automated Synthesis division.

Experience: Qualified candidates should have 5+ years previous experience in chemistry, mechanical engineering, or robosynthesis. Ideally, you'll have completed 10 (or more) previous multi-step total syntheses using 3D-Flow ModuloChem-XLs.

Software: Candidate should feel comfortable using the IBM SynBlox suite for fragment assembly, exploring GDB-23 for potential lead molecules, and assessing synthetic feasibility using the OPRD Engyn iPhone 9 app.

Special skills: Our synthesizers often require adjustments, thus experience in a trade - plumbing, welding, electrical - would be highly valued. Candidates interested in creating holographic "how-to" vidlets especially encouraged to apply.

Source: Burke Lab historical archives

#MyBigBreak Blog Carnival

Over at his place, Chemjobber has (unbeknownst to him, but knownst to us) begun a Blog Carnival around the topic of lucky employment breaks. Here's mine, albeit edited to protect names of the innocent...

My Freshman year at Big State University passed unceremoniously, as many do. Made lots of cultural and personal adjustments. Some courses aced, some classes ignored, all in pursuit of a major I thought I enjoyed. Enter Sophomore year, when I had the standard eye-opening, life-altering epiphany all self-identified organikers have upon taking O-Chem 201. But that's not where My Big Break(TM) occurred.

Fast forward to the weekly Chem Colloquium, in which speakers from the outside world came in to advise we burgeoning chemists how life looked on the other side of college. Once, a wild-haired, soft-spoken gentleman visited from the Big City. He worked in pharmaceutical chemistry, and I'll never forget something he said at the end of his talk: "Interns Wanted." Yes, we were being pitched to finish his presentation! At that moment, years of summer toil checking bags, cleaning parking lots, mopping floors, updating registers,* sharpening pencils*, and preparing transparencies* paled in comparison to WORKING IN BIOTECH. I somehow bulled my way to the front of the lecture hall in time to grab the last open slot on his roster. 

The rest, as they say, is history... 

--
*This was before the Internet, tablet PCs, and wide adoption of PowerPoint. Ask your parents.

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

Wilder 'Chemistry' from 1880

What was the first mention of "Chemistry" in the journal Science?

You might think, given that Science started in 1880, that an author would first refer to 19^th-century champions such as Perkin or Wöhler. Perhaps they'd write of new fuels for transportation, electrochemistry, or the advent of large chemical industries such as BASF or DuPont.

None of these. On page 4, issue 1, famed comparative anatomist and professor Burt Wilder writes:

"A Bit of Summer Work: Notwithstanding the number of 'Summer Schools of Science' to be in operation this season, many teachers are likely to pass the vacation at a distance from the facilities afforded by organized laboratories. How shall they employ their time?  

. . .the teacher who hopes to make his instruction each year more thorough than the last, will be pretty sure to spend the remaining month or two in the search of help from books, and, while regretting the vagueness of the information thus obtained, may seldom think of making it more real by personal observation. 

Now it is true that in some branches of science this may require appliances not readily obtained. This is the case with Chemistry and Physics, and some parts of Natural History. But Botany and Entomology may be pursued almost under any circumstances, and I venture to suggest that at least one kind of anatomical work may be carried on with but a slight amount of apparatus."

Wilder's cure for teachers' potential summer slacking? Purchasing "a very sharp knife, and a pair of 'wire-nippers'..." - all the better to study the (freshly-dissected) brains* of cats, sheep, dogs, and rabbits. He closes his essay with this potentially tongue-in-cheek phrase:

"If this is done, by the end of summer the teacher will have become better able to appreciate the peculiarities of the human brain when one comes in his way..."

*Pssst! Did you need instructions for that? Wilder generously provides an address at Cornell where one can obtain hectograph (printing by means of aniline dyes and gelatin plates) copies of cat dissection protocol.

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"

Confusing 'Chemistry' Image of the Day

This image appeared in an NPR Shots blog post outlining the CDC's recent recommendations on male circumcision:

Source: NPR News / Corbis Images

Please help me understand - What on earth do the floating molecules have to do with this story? 

I grok that the image suggests two men deep in conversation. The article doesn't mention any drugs. Nor bodily substances. No pheremones, hormones, biomarkers, or viral particles enter the conversation. Just another case of stock images gone wrong?

Candid Chemistry - 2014 Edition

Occasionally, readers will send me funny pictures that somehow capture the chemistry cultural zeitgeist. Here's some from the last few months:

At MIT, you can apparently chain your bike to a caffeine molecule!

Seen at UC-Berkeley: the ultimate chemical Doom tribute
(...to this guy)

Still frame from LeVar Burton's charity read of Go the #*&@ to Sleep
Does anyone recognize the (fake) elemental symbol poster? Geordi would never approve.

Attn, Chemjobber: from Austria, a promotional poster extolling the virtues of chemical employment!
(and a hip song to go with it!)

Heartfelt thanks to everyone who sent one in. Keep 'em coming!

(seearroh_AT_gmail)

Help Wanted: "Working Hours" Survey

Ofer Kedem, a postdoctoral researcher in the Weiss lab at Northwestern, has posted a survey to try and get a handle on the daily grind for academic chemists. He and his colleagues hope to garner enough data to publish their results in an open-source journal.

In the interest of statistical significance, won't you help them out?

HERE'S THE LINK.

(Thanks!)

Cubanes! Get Your Cubanes, Here!

A cube of med-chem cubanes**

It's not often you see drug candidates advanced with cubane substructures.* A collaborative group from the UK branch of AstraZeneca and Oxford University aims to change that: a report in Organic Letters indicates they've produced gram-scale quantities of cubane derivatives with common med-chem handles already "baked in."

Starting from a 1,4-cubane diester, Burton, Davies, and Wlochal take turns elaborating each side into thiazoles, beta-diketones, nitriles, amine salts, and ynones. Though more cautious readers might expect the cubed synthons to go up in smoke, they actually seem to survive fairly rigorous conditions - boiling water, phosphoryl and oxalyl chloride, TMS triflate, LDA.

I'd be most interested to hear from any readers who integrate these new building blocks (sorry, couldn't resist!) into their research. It's hip to be...cubic.

* On Twitter, CJ (rightly) points out that the authors could have done some DSC (stability) and solubility assays, just to put minds at ease that these synthons really could be integrated into a drug campaign.

**Not a real substance (but wouldn't that be something???)

A Chempubs Hat Trick

Slow down, Guangbin!
(said I, channeling my inner Dr. Freddy...)

Guangbin Dong of the University of Texas-Austin has just published three papers in three different journals with Impact Factors over three. What's more - he did it all in the same week.

Just think of them as buckyballs

The papers in question?

"Regioselective ketone alpha-alkylation with simple olefins by dual activation"
Science, published 4 July 2014; 2013 IF: 31.0

"Cooperative alkylation of cyclobutanones and olefins leads to bridged ring systems by a catalytic [4+2] coupling"
Nature Chemistry, published 6 July 2014; 2013 IF: 21.8

"Alkylation of rhodium porphyrins using ammonium and quinolium salts"
Organometallics, published 7 July 2014; 2013 IF: 4.1

I hereby institute the Chempubs Hat Trick - Three papers, Three Journals, IF > 3.0, one week.

Congratulations to Prof. Dong for winning the inaugural award! But, I'm sure I've missed others who've been so deserving. Readers, have you noticed anyone else - present OR past! - who made this many simultaneous "shots on goal"?

Leave awardees' names in the comments!

Friday Fun - Big Plans

Only five weeks to go until ACS San Francisco! Who's excited?

An Acme Labs product

(With gracious nods to the ACS and Dr. Leuenberger for their long-suffering patience and hopeful humor...)

Happy Friday,
SAO

Best. TOC Graphic. EVER.

From Acc. Chem. Res., a true gem. You're welcome.

P.S. - If you've never seen it, try the TOC-ROFL Tumblr!

Friday Fun: Posters

Two regular readers have sent in chem-themed posters from different ends of the U.S.A.

First, from Lockheed Martin, comes this educational reminder:

Not unless he wears safety gloves, he won't!

Then this advertisement for Harvard Summer school, seen on mass transit:

Psst! We just tell 'em it's a lot easier in the summer...

Happy Friday,

See Arr Oh

JLC at ACS San Francisco this August!

Costume Craze | Sent by Carmen Drahl

I've finally booked the tickets! 

Excited to attend my first ACS Meeting in a looong while.

I'll try to tweet updates from a few of the sessions using the #ACSSanFran hashtag. 

Look for me in the crowds! 

(see registration photo at right)