ChemBark

I don’t know why I find myself writing so many posts about happenings at Columbia, but I do. And the trend continues, thanks to this ad I found on page 84 of the March 18th edition of Chemical & Engineering News:

The ad begins:

THE DEPARTMENT OF CHEMISTRY seeks to appoint an Associate in Discipline beginning July 1, 2013, for our busy undergraduate laboratory programs. This is a full-time special instructional faculty position with multiyear renewals contingent on successful review…

An Associate in Discipline, you say? Great. I can think of a few chemists at Columbia who need to be disciplined (1 2)…

Yes, you read that title correctly: Jean-Luc Picard, the greatest starship captain of all-time, failed organic chemistry at Starfleet Academy. In his defense, it was probably less to do with intelligence and more to do with being distracted:

I pulled that video clip so I can show it to my students during our opening lecture. It should go well with the “How to Win Orgo” handout.

Update (5/1): Thanks to a tip in the comments from “bad wolf”, I went and pulled a clip from Star Trek: Generations where it is revealed that one of Picard’s ancestors won the Nobel Prize in Chemistry. It makes his failure in orgo all the more astonishing.

It looks like someone is using the deadly nerve agent sarin in the ongoing civil war in Syria, which may very well draw the United States into the conflict. I did a project on sarin for a class in my sophomore year of college at NYU. Here is the handout I prepared to accompany my talk.

Looking back on the document, a few things stand out:

1. It’s amazing how simple of a compound sarin is.

2. I had bizarre taste in fonts.

3. I’d forgotten I had written about Osama bin Laden a full year before the attacks on 9-11-01.

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.

Here are some nice reads to get you depressed about a career in academia.

1) Last week, The Crimson published a wonderfully deep look into the process of getting tenure at Harvard.

“The ad hoc process is greatly shrouded in mystery; remarkably little is written about it,” says current Senior Vice Provost for Faculty Diversity and Development Judith D. Singer. She smirks wryly as she swigs coffee from her mug, as if this is something she’s explained a hundred times before.

“What the ad hoc process does is it takes a recommendation that has come up out of a department, been through a dean, and says, ‘Let’s look at this with a fresh set of eyes. Let’s look at the totality of the evidence and make a dispassionate decision about whether the recommendations that have come up are really in the best interest of the University,’” says Singer.

In addition to the dossiers and area experts, the committee brings in a set of witnesses from the candidate’s department, typically the department chair and the chair of the committee that did the promotion review, among others. As the witnesses arrive at half-hour intervals, they see the membership of the committee for the first time. Until that point, the identities of the panel—except, of course, those who are ex officio—are kept confidential to prevent advance solicitation.

and…

The cases are rarely cut and dry. Negative witnesses are often called in to dissent the promotion. “Even in a canonization there’s a devil’s advocate,” says Singer, “and that’s part of what the ad hoc process is designed to do: to raise all of the questions and say, ‘Are they of sufficient concern to not make a tenure appointment?’”

The ad hoc is the mostly anonymous end to Harvard’s tenure process—when the dozens of classes and published papers boil down to a single decision. Many tenured and tenure-track professors say the process is unfair, that it is too subjective, too anonymous, and too unpredictable. But fairness may be beside the point. Those familiar with the process say Harvard is not interested in promoting good junior faculty, but rather in making sure it has the very best.

Quite a few very successful chemists were formerly assistant professors of chemistry at Harvard (who left for a variety of reasons). Steve Benner is one of my favorites.

2) Earlier this month, Slate published an essay by a humanities graduate student about how going to grad school was a huge mistake for her.

Don’t do it. Just don’t. I deeply regret going to graduate school, but not, Ron Rosenbaum, because my doctorate ruined books and made me obnoxious. (Granted, maybe it did: My dissertation involved subjecting the work of Franz Kafka to first-order logic.) No, I now realize graduate school was a terrible idea because the full-time, tenure-track literature professorship is extinct. After four years of trying, I’ve finally gotten it through my thick head that I will not get a job—and if you go to graduate school, neither will you.

I know the situation is different for students in the sciences, but I think some of her experience is still applicable. Here’s a more charitable assessment of going to graduate school in the sciences from last year, also in Slate.

3) Finally, an oldie but goodie from 1999: “Don’t Become a Scientist!”

Why am I (a tenured professor of physics) trying to discourage you from following a career path which was successful for me? Because times have changed (I received my Ph.D. in 1973, and tenure in 1976). American science no longer offers a reasonable career path. If you go to graduate school in science it is in the expectation of spending your working life doing scientific research, using your ingenuity and curiosity to solve important and interesting problems. You will almost certainly be disappointed, probably when it is too late to choose another career.

While I like Professor Katz’s piece, it should be noted that the man certainly has some strange opinions.