Archive for the ‘Hall of Shame’ Category

“What’s Wrong with this Picture?” — The Return

Friday, October 5th, 2007

Hello friends.  Remember me?  It’s your ol’ buddy, Paul Bracher.

You’re probably asking yourself, “What brings this guy back from the dead?”  Well, when a postdoc in our lab showed me what arrived in the mail, not only did I roll over in my grave, I decided to resurrect everybody’s favorite chemistry game: “What’s Wrong with this Picture?”

The following 52-page brochure arrived courtesy of Oxford University Press with the following cover.  That’s right…COVER:




Oh. My. God.  The real question is: What’s right with this picture?  Not much.  There are messed up bond angles, aryl Texas carbons, acyl Texas carbons, Rhode-Island carbons, bizzare peroxides, Texas oxygens, Texas nitrogens, and the list goes on.

What the hell is wrong with these people and why the hell is the ACS logo on this piece of garbage?  The O.U.P. editors should be drawn and quartered, and their heads should be displayed on pikes outside of ACS headquarters in Washington.

As if the front cover didn’t offer enough entertainment, the back cover has the following unintentionally humorous statement:

xford (sic) University Press, Inc. publishes works that further Oxford University’s objective of excellence in research, scholarship, and education.

Hooray for excellence.  Anyway, this weekend I’ll probably post on the upcoming Nobel Prize announcement (Oct. 10th).  After that, I might go back into hibernation.  We’ll see.


Mistakes and Mnemonics

Wednesday, July 4th, 2007

An astute reader passed along the following nomination for the official Chemistry Hall of Shame (accept no imitations).  It’s another chemistry advertisement, published on page 66 in the June 18th edition of C&EN:

An Ad for Iodosuccinimide in Chemical and Engineering News

Sweet. I guess if you buy two methylene groups, they’ll throw in an extra one for free.  Big props to J. for scanning in the ad and passing it along.

All this succinimide/glutarimide business reminds me of my favorite chemistry mnemonic—the one for remembering the straight-chain diacids (from two carbons to seven):

Oh My, Such Good Apple Pie

(Oxalic Malonic Succinic Glutaric Adipic Pimelic)

Now, I’m not going to do something as hackneyed as ask, “What is your favorite chemistry mnemonic?” Nope. Not going to do it.


You Smelled What?!

Tuesday, April 17th, 2007

From last week’s Harvard Police log:

6:11 p.m.—A Harvard University Police Department (HUPD) officer was dispatched to a report of a suspicious odor in Jordan Hall South believed to be carbon monoxide in the building. The officer met with the reporting party who stated that while working in the building they smelled a strong odor and began to feel sick so they pulled the fire alarm to evacuate the building. Cambridge Fire Department tested the air quality which came back negative for carbon monoxide and deemed the building safe for re-entry. The reporting individual was treated by EMTs with oxygen on the scene and refused any further medical assistance.

Some people at Harvard are so talented they can smell carbon monoxide, an odorless and tasteless gas.  I’d like to see someone at Free University of Berlin do that.

And pay no attention to the item where an officer caught two guys smoking weed and just let them go.  Carry on, good sirs.


The ACS Has Ruined Black History Month

Monday, February 26th, 2007

Ready for another round of what’s wrong with this picture?  Good.  Take a look at this ad for ACS Publications that ran in the last edition of C&EN (Feb. 19, p. 33, click for full image):

I’m not particularly upset that Dr. Julian isn’t wearing gloves, and I’m not going to whine about the bright sources of light in the background that make this an awful photograph.  This time, my beef is with the caption:

In 1948, Percy Julian developed a new way to synthesize hydrocortisone, which is still used to treat rheumatoid arthritis; 45 articles published by Julian are in the ACS Legacy Archives.

As far as I know, Julian never came up with an original synthesis of hydrocortisone (or cortisone, for that matter).  What Julian is famous for making is Reichstein’s Compound S, which Upjohn later found a way to oxidize to cortisone using a microorganism.  In fact, once Upjohn discovered the process for selective oxidation at the 11-position, there were many routes to cortisone, not just through compound S.  Julian’s route through steroids isolated from soybeans was not as effective as Syntex’s route through the Mexican Yam, since this species of yam produced a greater yield of the steroid precursors.  Julian eventually quit his job as director of the Soya Products Division at Glidden so that he could work with the Mexican Yam.

While we’re busy correcting things, the 45 articles by Julian that the ACS claims to have in its “Legacy Archives” include two addition/correction notices.  Thus, the correct value for the number of articles he published with the ACS is 43, two of which he later amended.  Feel free to check my math.

So, let’s recap:

1.  Julian did not make hydrocortisone in 1948.   He reported the partial synthesis of Compound S in 1951 (submitted to JACS in 1950).  I don’t know what 1948 has to do with anything.

2.  Julian never came up with an original, complete route to hydrocortisone.  Upjohn’s fermentive oxidation of the 11-position of steroids made it possible to take Julian’s route to Compound S all the way to cortisone.  This process was developed in 1951/2.  (Although he did not make the key discovery, Julian should be praised for predicting that this amazing transformation would eventually be discovered.)

3.  Julian/Glidden applied for a patent on the “Preparation of Cortisone” on September 9, 1950, but it was one of those pie-in-the-sky deals.  They never actually made the key transformation, and basically said so in the patent: “The present invention is not concerned with the introduction of the 11-keto group, nor with the formation of the acetyl group in the 17-position of the molecule, but is concerned with the other conversions and reactions mentioned.”

3b.  In light of this important fact, it is amazing that Julian was inducted into the Inventor’s Hall of Fame for this particular patent.  Why not choose one of his many other inventions?

4.  The ACS Legacy Archives contain 43 (not 45) articles by Percy Julian.

Do not leave with the wrong impression; Percy Julian was a truly excellent chemist.  But the fact that the ACS didn’t even bother to get its facts right suggests that this full-page ad was more about pandering to a perceived need to participate in Black History Month than about honoring an excellent chemist.  In the future, I hope that the ACS publishes an ad that accurately reflects Julian’s wonderful contributions to our field, and I hope it doesn’t wait until next February to do so.