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Who Says Chemistry Isn't Fun?
I DASH T H R O U G H THE LOBBY OF T H E American Chemical Society head-quarters at least twice a day and rarely pause to notice a table of ACS journals by the front door. But one day last week was different.
I slowed down long enough for my eye to fall on the cover of the March 8 issue of the Journal of Organic Chem-istry. I picked up the journal and thought: "This cover has a playful feeling. It looks like something Roald Hoff-mann would do."
Turning inside, I was only mildly surprised to find that the lead article was, indeed, by Hoff-mann, a Chemistry No-bel Laureate and poet, and postdoc Dean J. Tantillo. The cover features transition structures for one of several molecules, termed "fickle hexadi-enes," shown above a stylized potential energy surface adorned with a verse from Shakespeare's Sonnet 126, thou, my lovely boy, who in thy power/Dost hold Time's fickle glass, his sickle, hour."
How does an article like this come about? And how does it end up adorning the cover of one of ACS's most prestigious journals? I started with Hoffmann.
He laughed when I called and told me this story "This is a weird paper for me because there isn't a single orbital in it, no metal atom... and it's short. It takes me back to my organic days," he said. "Recently, a wonderful postdoc, Dean Tantillo, from Ken Houk's group at UCLA, came to work with me. Naturally, he loves organic things. I pulled out a paper that I had submitted to the Journalofthe American Chemical Society in the spring of 1967"
In that paper, Hoffmann drew 37 intriguing molecules, each illustrating some bonding principle. JACS rejected it. "I suppose it got turned down because it was just speculation, not even a calculation in sight," Hoffmann said. "For some reason, I was not persistent in getting it into print. But when Dean came, I showed him this paper."
In theJOC paper, Tantillo and Hoffmann examine two molecules from the rejected paper. "The Cope rearrangement," Hoff
mann explained, "is a prototypical concerted reaction. In principle, it can proceed through 'chairlike' and 'boatlike' transition states. Normally the chairlike process is lower in energy, but we have come up here with some interesting polycyclic hexadi-
enes in which the 'boatlike' transition state is quite competitive, as they say, with what might have been thought to be the favored 'chairlike' one. Ergo their fickleness. Not earthshaking, but great fun."
But how to illustrate this? Enter JOC Editor Dale Poulter and Senior Editor Cindy Burrows of the University of Utah, and Associate Editor Bob McMahon of the University of Wisconsin,
Madison. When the article came in and was reviewed, they all thought it might make a nice cover. Tantillo came up with the design and one verse, Hoffmann suggested an alternative, andJ^OC staff artist Linda Mae Mattingly took the finished art and turned it into a cover. Mattingly works closely on covers with Senior Associate Editor Mary Beth Harig in ACS Journals Publications, in Columbus, who in turn oversees JOCs production. Like Hoffmann, everyone used the word "fun" in describing what they do.
Research has a serious purpose, but I've always thought that if someone is going to spend 10 to 12 hours a day doing something, it should also be fun. Poulter, who succeeded Utah's Peter Stang (now editor ofJACS) and has only been JOCs editor for a few months, is of a like mind. "The organic community is fun to work with, the authors and the reviewers," Poulter told me. "We want the best of organic chemistry published in JOC, so with the covers, we want to have fun but also visually tell people about the tremendous diversity of organic chemistry."
What can I say except this: Poulter is off to a great start, and Hoffmann has returned, albeit briefly, to his organic days. Who says chemistry isn't fun?
Views expressed on this page are those of the author and not necessarily those of ACS
H T T P : / / P U B S . A C S . O R G / C E N C&EN / MARCH 1 8, 2002 5
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EDITOR'S PAGEWho Says Chemistry Isn't Fun?