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:
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.
