ChemBark

Tom Barton won last year’s ACS national election for President (and was kind enough to answer our questionnaire about important issues facing the society). Yesterday, President-Elect Barton asked that I share this message with the readers of the blog:

In my ACS presidential year of 2014 I’m considering hosting a symposium on fracking with, of course, emphasis on the involvement of chemicals.  I would appreciate hearing from anyone suggestions for particular areas for inclusion, and potential speakers.  I seek a balanced set of presentations from experts in the various aspects, and would certainly be interested in any germane research.  I myself am not an expert in this arena, but I am trying to get smart in it.  In advance, I appreciate your assistance.

Feel free to weigh in using the comments. I will leave the first…

The Capitals beat the Maple Leafs yesterday, which for some strange reason made me think about what a great time I had at my first scientific conference, in Toronto. It was a meeting of The Electrochemical Society, and my labmates and I gave talks in a session devoted to electron transfer in functionalized fullerenes.

Things seemed so pure to me back then, well before layers of skepticism and cynicism caked onto my core love of chemistry. I had just finished my sophomore year at NYU, and I was scared as hell about giving my first talk. You can see my slides here, but this all took place in the era before slide presentations on LCD projectors were standard. I had to print the file onto transparencies at Kinko’s and carry them along on the trip.

I can vividly remember giving my first practice talk in front of the guys in lab. I thought my pace was fine, but I had rushed through what was supposed to be a 20-minute presentation in less than 10 minutes. This compounded my fears, so in addition to two more practice runs at NYU, we all went into a speakers’ ready-room at the hotel in Toronto and practiced again on site. Our typical conversations that day focused on how many spare pairs of underpants we thought we’d need to bring along to our talks.

At the session, I can remember my friends and I smacking each other to point out famous chemists. Fame is a relative term, but these people were all famous to us because we’d read so many papers about porphyrins and fullerenes. They were the titans of our world. “Oh my God…that’s Jean-Francois Nierengarten!” Dirk Guldi, another prolific author in our field, presented in a three-piece suit. Fred Wudl was there, and I believe Luis Echegoyen, too. It was like sitting in the front row of a rock concert. “Hey man! I read your papers!”

I can remember nothing of my presentation besides having to peel each transparency out of my purple three-ring binder before laying the sheet down on the blindingly bright projector. I made it through in great time, and mercifully, the questions focused more on the synthesis than the photophysics. I was much more comfortable with the former. I chuckled when I went back through the presentation and saw this slide:

Those columns were my life. You’d run reactions that would turn dark, then you’d add a bunch of DDQ and they’d turn even darker—jet black. At this point, you’d have to fish out your miserable (sub-10%) yield of porphyrin from amongst grams and grams of crap. I’m sure none of the PIs cared about how much these columns sucked, but Little Me cared deeply enough to use my nifty digital camera to snap a pic and make a slide out of it.

Also in hindsight, I can’t believe I omitted the hydrogens on my aldehyde functional groups. I hate it when people draw naked carbonyls:

The conference was much easier to enjoy once our presentations were done. I can remember several of the other talks and getting excited about some of the supramolecular chemistry being done. My friends and I also got to see a bit of the city, including the CN Tower and a Blue Jays’ game where Pedro Martinez was the starter. We sat on the first-base line, and the movement on his pitches was unbelievable.

Perhaps inspired by the night out—and since we were able to finally place faces/bodies with the names we’d seen in papers—my labmates and I decided to have a bit of fun. We drew a baseball diamond on a piece of paper and slotted the professors into positions and a batting order based on how athletic we thought they were. We then anonymously posted the sheet on the bulletin board outside the presentation room. I can remember the bosses crowding around it and complaining about their assignments.

And, perhaps this was the first time that I saw how these “adults” were not much different from the rest of us. I’ve never been as excited about a conference as that one, and I don’t think I ever will be.

Perfectionists take note: even titans of catalysis make embarrassing mistakes with their chemistry. Just look at this little oopsie that was caught by an astute reader in the Midwest.

It seems like there might be a bit of confusion hanging over the chemists developing methods for anti-Markovnikov hydroamination of alkenes at the Center for Enabling New Technologies Through Catalysis (CENTC):

Ummm….yeah….that’s not the difference between Markovnikov and anti-Markovnikov addition.

Those of you who’ve taken sophomore organic chemistry will remember that Markovnikov’s rule states that protic functional groups (e.g., H-NR’R') will typically add to double bonds such that the hydrogen adds to the less substituted carbon (and the other group, e.g., -NR’R', adds to the more substituted carbon.) What Hartwig and coworkers have drawn as the Markovnikov product is still anti-Markovnikov. The products they’ve drawn might charitably be called conformational isomers, but they’ve failed to note any 3-D structure.

Of course, the true Markovnikov product would place the amine on the same carbon as the R group.

Hey, look what the American Chemical Society produced for St. Paddy’s Day: it’s a tutorial on the chemistry of alcohol, including its effects on your body and how your body attempts to rid itself of the poison.

Uh oh, but there’s a WWWTP? in there. If you pause at the 2:45 mark, you can see that they flubbed the structure of “amyl alcohol”:

While there are several isomers of amyl alcohol, instead of drawing one of those, the ACS has shown the structure for isoamyl acetate (commonly known as banana oil). When banana oil is dilute, it kind of smells like Juicy Fruit bubble gum. In concentrated form, it smells really gross. I know, because I made it in 6th period orgo lab in high school and the people around me in 7th period religion paid the price.

But good effort, ACS! This is exactly the sort of info we (as chemists) should be communicating to the People. It’s news they can use. Of course, in the future, try to get the structures right! (And for the record, you also misspelled “judgment” at 0:49. Boo.)

H/T to Kim the Magnificent for the tip.

My friend Roger was searching for—well, I don’t know what he was searching for, but this is what he found:

That is from the Web site for the Biochemical Journal, which the editors have decided to call “BJ Central”. There’s also “BJ Mobile” among a group of other specialized BJ sites. I particularly enjoy the menu option labeled “Submit to BJ”.

This set of abbreviations is much less subtle than the two previous front-runners on the puerility scale, PNAS and Anal. Chem. Are the editors really that oblivious?