June 15, 2012
I was flying home from Europe yesterday and was watching the Oscar award-winning movie “Good Will Hunting” starring Matt Damon, Robin Williams, Ben Affleck, and Minnie Driver:
One thing I missed the first time I saw the movie, was a moment where Matt Damon’s character shows up at Minnie Driver’s dorm room to ask her out on a date. She complains that she can’t because she has to spend the whole night attempting to assign the 1H NMR spectrum of Ibogamine:
SKYLAR: Oh, I can’t.
WILL: All right.
SKYLAR: Oh no, I didn’t mean I can’t, like, EVER, I just, can’t right now. I’ve got to assign the proton spectrum for ibogamine. Although it sounds really interesting it’s actually fantastically boring.
WILL: All right, Um…
SKYLAR: Maybe some other time.
Of course, Will Hunting, janitor for MIT, and genius, goes off to the park and quickly scribbles down the structure on a little piece of paper along with his proposed 1H NMR assignments. Who needs the actual spectral data?
For those that don’t know, this movie was very critically acclaimed. It received 9 Oscar nominations and won two, most notably, best original screenplay. So the moment the plane landed I was intrigued to look into how much homework Affleck and Damon did to ensure the validity of that one minute plot line. Too often we see foolish and non-sensical science in movies and on TV. The fact that he assigned the spectrum without even seeing the data aside, I didn’t recognize the name Ibogamine off the top of my head, so my first search was whether this compound even existed. A quick check in the ACD/Dictionary, and here it was:
Next question, was whether the NMR would even be difficult for this? Then searching our database for NMR assignments, I found the 13C NMR assignments for two forms:
Unfortunately, no 1H NMR assignments to be had though.
But, after a little more browsing through the web, I came across a Yale Professor who created this very problem for his class based on the reference in the movie:
Check out Problem #6 here:
And furthermore, it turns out to be a reasonably complex 1H NMR spectrum:
And based on the spectrum above, we get a reasonable looking 1H NMR prediction:
So a couple of things on this fun Friday:
1) Kudos to Damon and Affleck for incorporating NMR into their script, a critical piece of Organic Chemistry, that often doesn’t get the lime-light. I think it’s pretty obvious they consulted a chemistry-savvy person for this one.
2) NMR predictions and databases might not only help you with your structure elucidations, but they also might enable you to land a date with someone completely out of your league 🙂