Meet Quindolinocryptotackiene

Tony over at ChemSpider takes us on a trip down memory lane to one of the most successful stories surrounding Computer Assisted Structure Elucidation (CASE).

It is also the best example of achieving symbiosis between a spectroscopist (in this case Gary Martin) and software (ACD/Structure Elucidator) I have ever seen.

He is referring to "Solving a structure computationally after 10 years of human effort" that was presented by Gary and Tony at the ASP Meeting in 2003 (It's a long presentation but skip to slide 44 to get to the meat of the presentation).

There is also a publication on this story. 

Tony's purpose for resurrecting this story is as follows:

Now, we THINK we have it elucidated correctly. However, we would like to confirm it. Synthesis of the molecule in question, further NMR data generation and a crystal structure would help finish this work fully. This is a call to organic chemists to participate in a hobby project. Anybody want to help? We guarantee a publication etc. The structure is shown below. Contact me at antonyDOTwilliamsATChemspiderDOTcom. Thanks!

Hopefully someone is willing to step up to the plate.

I'd also like to take this opportunity to, once again, point out that CASE is not simply about piling a bunch of data in a piece of software and getting the answer out the other end. Sure this is possible, but it usually benefits when an experienced spectroscopist works with it and shares their knowledge of the existing chemistry. I think Gary's story is a perfect example of that.

That being said, in Gary's case, along with comments I have received from Dr. Shaun Tennant (another elucidator user) in the past, the software is an unbiased approach that will propose some things that the spectroscopist simply might not think about. Knowledge can sometimes be your enemy.

Comments

[Chris Singleton]

I wholeheartedly agree with Ryan's comment that 'CASE is not simply about piling a bunch of data in a piece of software and getting the answer out the other end'. Many people I have talked with were under the impression that CASE software is data in, structure out, and don't realize there is a whole host of parameters to input. A lack of understanding of them can result in no structure, or worse, an incorrect structure (though this is alleviated somewhat by ranking structures by their deviation from predicted CNMR). I get the feeling that there are those that think the software has a big red button that you push, and poof! Your results come out.

[Ryan Sasaki]

Thanks for your comments Chris and re-iterating my point from your own perspective.

Unfortunately, as we try and stress this as much as possible, it naturally turns people off from using software because it labels it as hard to use, or too time intensive.

I won't lie, the software is not easy to use, there is a learning curve and an adjustment period in using this software.

However on that note it doesn't need to be used for every elucidation. If it's an easy problem...don't use the software. Why bother enlisting in the help of software, if you can do it faster by hand? I think it's those difficult cases where the software really reaps rewards.

Of course this being said, the software isn't just elucidation software. So just because you aren't using the elucidation algorithms every time, you have access to NMR predictions (1H, 13C, and 2D), 1D and 2D NMR, MS, UV-IR, Chrom Processing and databasing, etc. to use to help with other verification and elucidation problems.