Archive for the ‘Chemmys’ Category

Now Accepting Nominations for the 2010 Chemmys

Saturday, December 18th, 2010


I’m resurrecting the Chemmy Awards from the old site, but this year I actually plan to finish what I started.  In order to keep things simple, the categories will be as follows:

Outstanding Achievement/Paper in Organic or Biological Chemistry
Outstanding Achievement/Paper in Physical, Materials, or Analytical Chemistry
News Story of the Year
Chemical Hero(ine) of the Year
Chemical Villain of the Year
Accident of the Year

Please use the comments to make nominations.  The award winners will be announced in the first week of January.

Organic Achievement of 2006: Pd(IV) Intermediates Might Not Be That Rare

Friday, April 27th, 2007

The Chemmy Award for Organic Achievement of the Year goes to:

Melanie Sanford (Michigan) for establishing that Pd(IV) intermediates are important in at least one class of catalytic C–H bond activation reactions

I had decided on the recipient of this Chemmy a long time ago but procrastinated on writing the citation. This weekend, commenter “tuna fish” mentioned that Dr. Sanford might be moving to Yale or Caltech, and while I have no idea if this is true, the comment reminded me of my fondness for her work and that now is as good a time as any to write about it.

First off, trying to “contain” the Chemmy achievement awards in the various chemical disciplines to one year (here: 2006) is going to be difficult, because cool discoveries often take time to develop and get noticed. In this case, Sanford’s C–H activation work can be traced back to 2004. It was only last year, however, that the picture became clear (at least, clear to me).

When I learned organometallic chemistry—way back in 2002—we were essentially taught never to invoke Pd(IV) intermediates in our mechanisms.  Pd(IV) was simply too energetically-inaccessible to be relevant in most cases. Along these lines, I witnessed the merciless ridicule of more than one student by the teaching staff for using Pd(IV). Instead, good boys and girls used the Pd(0)/Pd(II) couple in their mechanisms.

In 2004, Sanford came along and published a simple case of catalytic, chelate-directed C–H bond oxidation:

Instead of outlining a mechanism that shuttled back and forth between Pd(0) and Pd(II), Sanford proposed a mechanism involving Pd(IV):

Naughty!  Or so I thought.  A subsequent study essentially extinguished all doubt that the Pd(IV) mechanism was correct. In this 2005 JACS comm., the Sanford crew hypothesized they could change the system to stabilize the Pd(IV) intermediate, found they could actually isolate it, got a crystal structure showing that it was indeed a Pd(IV) species, and then showed that heating it gave the same types of products that they saw in reactions where the intermediate could not be isolated. Crystal structures are the closest thing we can get to having incontrovertible photographic evidence of what molecules are actually doing, so you can’t really argue this one.  Score one for Pd(IV).

I know a lot of the hardcore synthesis crowd isn’t enamored with this sort of C–H activation chemistry because it is chelate-directed, which limits the scope of the reaction. That’s true, but what makes this batch of work so interesting is not the synthetic utility as much as the scientific value. We gained a new appreciation for the mechanism at play in these reactions and had to reassess a long-held notion of what isn’t reasonable.

So, congratulations to Dr. Sanford and coworkers. Enjoy your Chemmy and keep the good work coming.  And if any of you donkeys out there thinks there was someone else more deserving of this award, feel free to register and start your own damn blog.


Outstanding Academic Department of 2006: Princeton University

Monday, January 8th, 2007

The Chemmy Award for the Most Outstanding Chemistry Department of 2006 goes to:

Princeton University

In the comments thread announcing the Chemmy Awards, Excimer noted that “although all these awards are subjective as hell, the Outstanding Academic Department is really out there. How can one honestly be 100% objective about such things?”

He’s absolutely right; there’s no way to definitively peg what department had the best year. This award was made to mimic how various sports leagues recognize a general manager or team executive of the year. We’re just asking, “which department made the best personnel moves or exceeded expectations for the past year?” Of course, this is going to make it harder for the “top flight” departments to win this Chemmy. The bar is higher for them, as we’ve come to expect schools like Berkeley, MIT, and Stanford to do amazing things.

So, why Princeton? They’ve made a number of big strides forward in the recent past. Coming on the heels of Sorensen’s arrival from Scripps in 2003, Princeton was able to attract superstar David MacMillan this year. Princeton also gained a resident chemistry blogger in 2006, Carmen Drahl, who’s noted that the school has vastly improved its instrumentation this year. A new chemistry building is also in the works, with completion scheduled for 2010.

In terms of losses, the sophomore organic class at Princeton might suffer with the impending departure of Maitland Jones. He is closing down research operations in preparation for a move to Greenwich Village to teach orgo at NYU. For those interested, The Chem Blog had a post this summer chronicling the movement of some other professors. Yale had a particularly rough year, which included the loss of Hartwig to Illinois.

So, when I think of up-and-coming schools, Princeton is the first that comes to mind. I’ll stand by it as deserving of the award for 2006, but feel free to post your thoughts on other departments that will soon be surging up the rankings.


Chemical Villain of 2006: Dalibor Sames

Monday, January 1st, 2007

After thorough examination, the Chemmy “Award” for Villain of the Year goes to:

Prof. Dr. Dalibor Sames for the Columbia C-H Activation Fiasco

The sad part of this post is not that Sames won, but that there were other legitimate contenders. The strongest cases could be made for Dalibor Sames, Bengu Sezen, and JJ La Clair. Some people might have also thrown R&D at Pfizer into the mix for ruining our stock portfolios, but that’s not really fair. The fact of the matter is that the system seems to have worked in the case of Torcetrapib—the drug’s danger was discovered in clinical trials and the project died. That’s life.

So, why not La Clair? Any other year he probably would have won, but in the end: 1) the hexacyclinol story was not as disgusting as the Columbia case, and 2) hexacyclinol has locked up the Chemmy in a different category.

The decision between Sames and Sezen was a tough call. If Columbia’s investigation shows that Dr. Ms. Dr. Sezen did naughty things with her data, you can bet that she’ll will run away with the Chemmy next year. For now—as is the custom in academia—the advisor takes home the award.

And I really think that Sames deserves it. Let’s review his credentials:

1. He retracted six papers and a significant part of a seventh. What chemist (besides Sezen) has ever had to do anything like this?

1a. If you think that Sames might be an “innocent victim,” please refer to Columbia’s policy on professional misconduct:

In modern collaborative research, the implications of academic misconduct or fraud go far beyond the individual; they also affect collaborators whose own work has been committed to objective search for truth. The specter of guilt by association may lurk in the background for many years to come. Therefore, joint authorship requires joint responsibility; each author claiming credit for the entire work must also be aware of joint discredit. Investigators in collaborative research projects each must make reasonable and periodic inquiry as to the integrity of and processes involved in gathering and evaluating data. It should be understood that overall responsibility for the integrity of collaborative research rests with the principal investigator. Senior investigators cannot be allowed to escape the consequences of the discovery of misconduct or fraud committed under their supervision.

2. The first round of retractions submitted by Sames had Sezen’s name on them without her approval or any indication that he was acting without her consent. (Note that JACS changed the wording of these retractions after publishing them—without making note of the edits).

3. While it has yet to be confirmed by Columbia, a lot of people have said that one or more students were essentially encouraged to leave (a.k.a. fired from) the Sames Lab for incompetence, at least in part because they could not reproduce the results that were eventually retracted. If someone in your lab raised questions about the reproducibility of an experiment, wouldn’t you feel obligated to check the procedure out for yourself? It’s not like Sames was that far removed from bench work; he easily could have run these reactions. Doing so probably would have prevented a lot of the subsequent mess.

4. When it became clear that something was wrong, Sames waited at least six months before publishing the retractions. Why did he wait if it wasn’t for her approval? Taking so much time was inconsiderate, as other chemists in the area of C-H activation wasted time trying to use Sames’ reactions (for example: Bellina, et al. Eur. J. Org. Chem. 2006, 1379).

5. Sames has publicly blamed Sezen in a variety of ways, such as in his wording of the retractions, in statements to news organizations, and by removing her from his lab’s Web page. While he was willing to fire these shots at her, when the press came calling to question him, he threw up his hands up and claimed that he’s not allowed to comment on the case due to the ongoing investigation. Either talk or shut up. Pick one. To do otherwise is unfair and cowardly.

There’s more, as you know, but you can use Google to refresh your memory. And if anyone thinks that this wasn’t a significant story, feel free to go crying to the editors of C&EN, Science, Nature, and the NY Times, too. The story is legitimate and newsworthy. If you don’t want to hear people talk about it, go somewhere else.

In fact, given the gravity of this particular story, I think we should consider including an actual prize with the Chemmy. Perhaps we can put Ed the Dog in charge of raising funds for an all-expenses-paid trip to Circle 8, Bolgia 8.

Who’s willing to chip in?


News Story of 2006: The Rise of the Chemical Blogosphere

Thursday, December 28th, 2006

The Chemmy for News Story of 2006 goes to:

The Rise of the Chemical Blogosphere

If you think this post is self-congratulatory, you’re damn right. But seriously, what the hell happened in 2006?

A few blogs, like Derek Lowe’s In the Pipeline, have been around for a while, and a few more showed up last year (e.g., Tenderbutton and my old blog). But look at the sidebar on the right. The vast majority of those blogs were born in 2006 and the list continues to grow. Organometallic Current and Levorotation, two blogs that look very promising, were just started in the past two weeks. Even the chemical media establishment is getting into the game with blogs from Nature, Chemistry World, and C&E News all appearing in 2006.

If you’re searching for the catalyst of the rise in blogs, look no farther than the Columbia scandal. After the school went into lock-down and C&E News chose not to cover the story immediately, chemists in search of information about the retractions turned to Google and found chemistry blogs. Communities started to grow around comment threads, and it became obvious to everyone that there are more than a few chemists willing to talk shop on the Internet.

While a lot of people are still wary about obtaining information on blogs, it’s clear that they have a legitimate place in both scientific politics and journalism. As scientists, we must actively seek new ways to improve the operational aspects of our field. An important tool in this plight is to study situations where the system failed. And in any democracy, decisions such as how tax dollars are spent ultimately rest with the electorate. Thus, it is important for the public to stay well-informed of current events. If chemistry blogs hadn’t provided a forum for the dissemination of the Columbia information, many people would never have found out about it.

Of course, this is just one of the many merits of chemistry blogs. You can turn to them to be informed, keep abreast of the latest literature in a niche area, get help with a problem, or be entertained. There’s something for almost everyone, and in cases where there’s not, a new blog is easy to start. While many of the blogs from the Class of 2006 may vanish, the chemical blogosphere is here to stay.