DOC Detective Work

I'd like to send some good vibes and a hearty hello to attendees at the 43rd Annual National Organic Symposium in Seattle. Wish I could be there with you guys; maybe I can 'save the date' for #44 in 2015.

While browsing around on the Division of Organic Chemistry website, I stared at the logo for one second too many, thinking "What molecule is that, anyway?"

Have you ever wondered that?

I figured that SciFinder would know best, so I searched for the exact carbon framework: Zero hits! So, it's not actually a molecule anyone's worked on. I poked around through ORGN's historical archives*, including the first N.O.S. program (1925, Rochester, NY). I perused the excellent recent review of the conference in JOC - no explanation there, either.

Let's examine a few of the other ACS Division logos. Fluorine chemistry stands out - some hand-drawn goodness representing a closed ampoule of the highly reactive gas:

Inorganic chemistry lays claim to the entire periodic table, with a lens flare for added emphasis:

My "Aha!" moment came upon viewing the coiled chain of the Polymer Division, suggestively curled back on itself to create a "P":

Go back to the DOC website, and have a peek at the tiny icon at the top of your browser tab. Here's how mine looks:

Get it? The graphic spells out the letters "D-O-C" (How had I not seen this before?!?)

Clearly, we've lost the thread of the joke due to better understanding of molecular structure. At its founding (1909), most Division members were still drawing what I lovingly refer to as the "Monopoly hotel" version of the cyclopentane ring - one bond artificially elongated to ease printing (or stenciling):

Over time, of course, we realized that a regular pentagon was a closer representation, and conformational analysis teaches that we ignore 3-D structure at our own peril. Nowadays, the more streamlined DOC logo - though structurally correct - loses the "D" flavor of the older generation's five-membered ring.

Challenge: We're still two years out from the next NOS meeting. In the spirit of olympicene, created to honor the 2012 London Olympics, perhaps someone could synthesize "ORGNANE," the presumptive hydrocarbon of our beloved logo. It's C12H22, so I doubt it's that volatile (ChemDraw predicts bp >200 deg C).

Hey SURF fellows, want to be famous? This might be the summer project for you!

*Fast fact: ORGN only claimed 1,014 members in 1948. This swelled to 16,800 by 2010, presumably due to the explosion in medicinal, polymer , and industrial chemistry research.

Chemical Nostalgia: Being the Mark

If you haven't read it yet, Paul's written a really great reminiscence about his first chemistry conference over at ChemBark. It's funny how reading someone else's account causes you to immediately flash back to your own "first time," especially since mine didn't go quite so smoothly...

I'll never forget my first pharma internship during the summer of my sophomore year. It was my dream job: smart people in pressed slacks, automated fraction collectors, a communal coffee pot, and (gasp) top-shelf Pentium II computers at work stations, equipped with (dial-up) SciFinder!

My boss wanted a coworker and I to present a poster at the big ACS meeting that summer. We would be one of about 400 posters on the floor, but I didn't care, I was going to go talk science with scientists. We stayed up late the night before, changing the poster layout* and gluing the backings down for each image; this was before cost-effective full-poster printing. I bought a new shirt and tie, and got a haircut. When the session came, I arrived an hour early to tack up my opus, and eagerly awaited the flood of potential listeners.

If you're familiar with poker, you know the expression "If you don't know who the mark is, you're the mark." That means someone's always at a disadvantage, and will likely lose all their money in fast order. Worse yet, the senior players know you're the mark, and take you down accordingly. With hindsight, it's clear to me: someone needed to present, but none of the staff scientists wanted to go, so they sent me.

I was the mark. And I got eaten alive.

"What's the platform?" "Umm..." "Any targeting groups?" "Maybe." "Tell me more about [pathway X]" "I think it has to do with cancer...?" "What's the SAR around that site?" "Lots of compounds."

My colleague was nowhere to be seen. I was on my own for most of those hours.

I'll never forget my intense embarrassment and nervous, hesitant answers. When the session ended, I just grabbed the poster and ran out of the room. Didn't go to any talks, didn't go back the next day. I'm sure my poster still sits at the company, buried under a pile of old journals.

*Fast forward a few years: my second poster had everything: color-printed on one rolled-out sheet, copies of abstracts and company contacts to give out to listeners, coached one-liners for questions, the works. That one went worlds better.