ChemBark

It’s time to start attacking the ChemBark mailbag. Let’s begin with this little gem sent in by Excimer:

Photo credit: Excimer

Excimer writes:

I’m currently reading the sci-fi classic series Cities in Flight by James Blish, and hooray! there’s organic chemistry in it. Unfortunately, it looks like this.

Indeed. You’ve gotta love the: (i) Texas carbon, (ii) doubly-bonded hydrogen, and (iii) calcium–carbon bonds. I guess this sci-fi classic is heavier on the fiction than the science.

There is nothing like a trip to my mailbox to bring a nice little blogging hiatus to a crashing halt. While attacking my pile of C&ENs, I caught this ad for TOSOH Organic Chemical Company on page 43 of the 11 June 2012 edition:

I guess the hair net and painter’s mask ensure that—unlike my Orange Chicken at Panda Express—these products arrive free of human hair. Matters of lab attire aside, what actually piqued my interest in the ad were the compounds for sale:

Sigh. That is not how I was taught to name organic compounds. My orgo professor—on the recommendation of IUPAC—told us to start by numbering the longest chain of carbons. Thus, 1-bromo-2-ethylbutane is properly named 3-(bromomethyl)pentane, and 1-bromo-2-ethylhexane should be 3-(bromomethyl)heptane.

Avid readers of ChemBark know that I love trick questions, and structures like the ones above make for great nomenclature practice. Many students will instinctively assume the carbon chain extending from left to right is the longest. When I taught orgo, I had to purchase red pens by the dozen.

Matt at ScienceGeist is hosting a blog carnival this week on “Our Favorite Toxic Chemicals.” The idea is to generate posts about chemicals that have reputations for being toxic, but that also have important applications and non-toxic manifestations (e.g., in low concentrations). All of your favorite chembloggers have posts up, including Excimer, who has returned from a long blog hiatus.

I should have my contribution up by Friday. What I love about this carnival is that the posts will live for eternity, standing ready to drop some knowledge on any curious soul who runs a Google search for one of these molecules.

In other news, I have been busy going around the department in preparation for a visit next week from a very special guest. On my recent travels from office to office, I came upon a number of these signs in the hallway outside of a research lab:

CHEMICAL FREE ZONE!!

NO labcoats, gloves, tlc plates, NMR samples or other chemical contaminants

The extra exclamation mark lets you know that they mean business. I’ll refrain from identifying the lab to protect my colleagues, but the scene definitely made me cringe. I understand it when marketers raise the “chemical-free” dagger, but a lab of chemists? Et tu, Brute?

In a subsequent discussion on the matter, a member of a different lab pointed out that my concern was probably a trifle, because this building was a laboratory not generally accessed by the public. Under these conditions, the sign is widely understood to succinctly communicate that contaminated items should not be brought into the office space.

While I think such an argument is tenable, it is preferable (and relatively easy) to avoid the controversy completely. If we—chemists—can’t be bothered to find a suitable alternative to “chemical-free”, then why should we expect the same from laymen? It seems like a sign that says “No lab equipment or samples in this room” would get the job done with only a slightly less economical use of words.

And finally, a kind chemical engineer sent me a link to the following paper, in which a freshly-minted Harvard professor railed against “chemical free” in 1995:

Chemistry and the chemical industry often are misunderstood by the general public. It is not uncommon for products to be advertised as “chemical free” or for a product to be labeled dangerous because it contains chemicals. As chemists, we know that these claims are incorrect. Unfortunately, many people in today’s society do not have the chemical training necessary to determine whether or not such claims are valid.

I guess J. Chem. Ed. was where bloggers blogged before there were blogs.

Part of the fun of having a blog is monitoring its traffic, and more traffic equals more fun. I say this because, eventually, someone is going to read this blog and finally create a respectable chemistry journal where all of the correspondence—including letters to the editor, original submissions, referee reports, responses to referees, editorial decisions, and reader comments—is signed and available online. That post was from 2007. What is the delay, people? Let’s make this happen.

Long ago, I had the fanciful idea of running an ad for ChemBark in C&EN. What better way could there be to reach out to so many chemists? Unfortunately, I quickly learned that I couldn’t even afford a single line in those mind-numbing walls of text at the end of the magazine. If you want an ad in the middle of the magazine, the minimum you’ll have to shell out is $3,560 according to this notice (16 April 2012, p. 54).

And what kind of magic was I expecting from an ad in C&EN, anyway? Oh yes…all 150,000+ readers would be so intrigued by a URL under a head shot of Ed the Dog that they would race to their computers and hit the site. Once they had the chance to read my biting criticism of Swiss department stores and admire my poor skills at Photoshop, they’d fall in love and become addicted to blogs, for sure!

Ummm, no. And it is through such a lens that I have wondered what other advertisers have hoped to achieve with expensive print ads—especially those who list random compounds they have available. I think my bewilderment hit an all-time high last month when this ad from Quanta BioDesign was published in back-to-back issues:

“Non-Quenching Fluorescein!” certainly grabbed my attention, and the first thing I felt compelled to do was look at the structure to see what was different about this fluorescein. That is when I noticed something was terribly wrong. At least, I think.

That’s not fluorescein, right? It has a methylene group where an oxygen should be. Wait, is that why this molecule is special? Wait, that shouldn’t even exist…it would tautomerize (such that one of the methylene hydrogens would move to the carbonyl group to make the ring system aromatic).

I was confused, so I went to the Web site and searched for Product #10885. It turns out, there is no product #10885.

So, let me get this straight…this company paid $6,150 (x at least 2 weeks) to run an ad with a wacky structure for a product that doesn’t exist?! I wish I had that kind of money to throw away. I’d save up and get Ed on the back cover.

I have found so many errors in ads run in C&EN that I could probably make a decent living proofreading them on commission. And I sometimes wonder how much money a chemistry blog could make if it wanted to get serious about selling ads. C&EN has a weekly circulation of ~164k and lists a rate of $6,150 for the ad above. Could a blogger like Derek Lowe, who reports traffic of 15-20k pageviews per day, make $615 from running that ad? Seems reasonable to me, and I’d just as well see people throw money at Derek.

Someone should run the experiment, but it won’t be happening here anytime soon. I purposely make sure I’m losing money on this site in an attempt to show I’m not in this for financial gain. That said, just to be on the safe side, I have still reported the blog to my employer as a potential conflict of interest. My job provides me with access to nice things like journals, which are useful to the blog and would cost a pretty penny if I were a professional journalist working from home. I think you can mount a reasonable argument that a revenue-free ChemBark meshes well with the educational mission of a non-profit research university.

Incidentally, the “ads” that you see running on ChemBark are fake. Several weeks ago, I added space for a 150 x 150 pixel image to the left sidebar and a 500 x 80 pixel image to the footer of the page. The ads that you have seen in these positions—for instance, the one linking to the assistant editor position listed at Nature Chemistry—have all been designed by me, for fun. They were neither solicited nor purchased, and I will continue to use these ads to link to things I like. Click them and warm yourself with the knowledge that no one is making a penny.

One of the perks of having a girlfriend with a broken leg is that she requires assistance in the shower, which I am happy to provide. In my extra time in the bathroom this week, I was horrified to pluck these inconspicuous containers from a lush forest of colorful beauty products:

Organic! Chemical free!            Wait.          Chemical free?!

Hmmm. It sure looks like there is matter inside these bottles, and I’ll bet this matter comprises chemicals of some sort. Why don’t we just take a look at the list of ingredients, shall we?

Nope, I was wrong. No chemicals. Just enzymes, vitamins, minerals, antioxidants, amino acids, and fatty acids. No chemicals here :/

I have blurred out the designer of these products because he is my girlfriend’s hairdresser and friend, and I don’t want an army of irate readers to descend on Los Angeles. That said, I have instructed my ladyfriend to relay my emphatic disapproval—in no uncertain terms—of the use of “chemical-free” to describe anything except a completely empty container.

Chemistry has all but completely lost hold of its brand in the sphere of public perception, and in today’s society, that can have disastrous consequences. In politics, parties actively try to sink their competitors by painting them in a negative light. Republicans never miss a chance to label Democrats as “the party that wants to raise your taxes”, while Dems counter that the GOP “only cares about the rich”. This childish back-and-forth is tiresome, but effective. That is why you see politicians jabbing and name calling at every opportunity the media grants them. It’s a vicious cycle, because if you decide to take the high road and not fight back, the negative slogans—whether accurate or not—will stick and seriously damage your brand.

Unlike for political parties, the science of chemistry has no natural enemies. Physicists aren’t going on TV to complain that dirty chemists are getting too much grant money. But, what is happening is that we have stood by while marketing agencies have hijacked and rebranded a few key terms from our jargon. For instance, they have imbued the term “organic” with all sorts of positivity and wholesomeness, while warping its definition from what chemists have historically understood “organic” to mean.

The case of “organic” might not be so bad, but the problem is unequivocally dire for “chemical”. In today’s advertisements, “chemical” no longer has just a negative connotation, it essentially denotes “toxic ingredient”. Somehow, one of our most generic terms—and one that lies at the very foundation of our profession—has been twisted into something dreadfully sinister.

How could we allow such a thing to happen? The answer is obvious: we have never fought back. While our field was maturing as a science and an industry in the 20th century, we proudly trumpeted the idea of “Better Living Through Chemistry”. DuPont even adopted the phrase as a company slogan…only to drop it in the 1980s. Since then, it is hard to point to a solitary example of a serious PR campaign on behalf of chemistry. In the meantime, we have allowed Madison Avenue to fill this vacuum by painting “chemicals” as bad in a wildly successful tactic for marketing consumer products.

In my mind, this is easily the biggest failure of the American Chemical Society, and to me, it appears that the ACS continues to do next to nothing to solve the problem. Chemists cannot count on chemistry and science to “sell itself”. While we know chemistry offers all sorts of benefits to society, we are going to have to load our weapons and mow down the booger-eating ad executives who are wiping the floor with us. The sustained growth and financial support of our field depends on it.

And incidentally, this is the sort of thing for which I pay ACS dues. While the matter is phenomenally important, I really don’t have the time, expertise, or resources ($$$) to mount a national PR campaign to promote our field. That said, I do have the time to campaign against apathetic ACS officers and candidates in the annual ACS elections. Mark my words: we’ll remember come November.

Aquí está mi lista de los cinco mejores químicos hispanos en la historia:

5. Andrés Manuel del Río – El descubridor del vanadio.

4. Luis Miramontes – Inventor del primer anticonceptivo oral (con Carl Djerassi y George Rosenkranz en Syntex).

3. Mario Molina – Demostró la amenaza de los CFC a la capa de ozono de la Tierra

2. Pedro Cuatrecasas – El padre de la cromatografía de afinidad y un químico médico muy bueno.

1. Severo Ochoa – Descubrió cómo los sistemas biológicos sintetizar ARN

0. Henry Eyring – El padre de la teoría de estados transiciónes nació y se crió en México, pero él era americano.