Wednesday, June 26, 2013

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.


  1. If the 6-membered ring is aromatic, a few people have bashed that one out before - time for some high-pressure hydrogenation!

    1. Good call! Get IBM on the phone for some AFM goodness, and presto!
      New logo.

  2. I'm not a fan of the awkward bond angles of the "C" part of the logo. For some reason it's really distracting to me. I'd much prefer if the "C" was canted a bit downward so that all the angles were 120 degrees like most drawn structures (and most of the rest of the logo) have.

    That being said, you could also just use a generic deutero alcohol fragment as a logo. You could even have it as part of a larger tertiary alcohol of some historic significance if you can think of one.

  3. That, um, fluorine logo...
    It kind of looks like a certain Internet meme. You know the one I mean.....
    I count myself very lucky not to have seen the original yet, put it that way.

  4. As a result of this posting, the ACS Organic Division has reverted to using the older version of the logo where the "D" is more prominent. It turns out the logo was "updated" in about 2007 while trying to make a high-resolution graphic for posters, NOS bags, and such. At that time, the leadership was unaware of the fact that the molecule was supposed to spell out DOC. As one senior DOC executive committee member recently wrote "I assumed it was a truncated steroid, which made historical sense. However it isn't because the ethyl and methyl aren't attached to the right places of what would be the CD rings." As far as I can tell, the first appearance of the logo was in 1985 on the NOS Program book; however, I would love to know the history of this including the name of the person who designed the original logo. I assume the use of the 2007 version of the DOC logo will continue to appear from time-to-time on various documents; however, those of us who have read this blog will be in-the-know on the correct version of the logo including why the molecule is there. In any event, I have added an FAQ on this on the Organic Division's website and I/we thank you for your detective work.