Copyright©2009 Antony Williams
About a decade ago I sat with my soon to be friend Gary Martin. Gary is larger than life. Literally. Tall, heavy, highly published, respected, damn funny, disruptive in a good way and one of my best friends. Gary is an incredible NMR spectroscopist and has contributed more to small volume NMR than any other NMR jock (in my opinion). We were in Florida at the ENC conference and I took Gary for a couple of cocktails and told him about my idea for an automated structure verification software platform that would verify suggested structures using NMR data…initially 1D NMR spectra and ultimately a combination of 2D data also. Then, the ultimate goal would be to automatically elucidate chemical structures from a combination of spectral data. It was a “napkin” plan where he and I signed our names to what it would take to do it. Over the next 10 years we would work together to execute on this plan as he moved from Pfizer to Schering Plough. The technical team at ACD/Labs would improve their software for analytical data processing, for multinuclear NMR prediction and for computer-assisted structure elucidation. Part of that development was using a combination of 1D and 2D HSQC spectra to verify structures and resulted in the publication below…
Automated structure verification based on a combination of 1D 1H NMR and 2D 1H–13C HSQC spectra, Sergey S. Golotvin, Eugene Vodopianov, Rostislav Pol, Brent A. Lefebvre, Antony J. Williams, Randy D. Rutkowske and Timothy D. Spitzer, Magn. Reson. Chem. 2007; 45: 803–813, DOI: 10.1002/mrc.2034
The paper described a method for structure validation based on the simultaneous analysis of a 1D H NMR and 2D 1H–13C single-bond correlation spectrum such as HSQC or HMQC. When compared with the validation of a structure by a 1D HNMR spectrum alone, the advantage of including a 2DHSQC spectrum in structure validation is that it adds not only the information of 13C shifts, but also which proton shifts they are directly coupled to, and an indication of which methylene protons are diastereotopic. Using multiple real-life data sets of chemical structures and the corresponding 1D and 2D data, it was possible to unambiguously identify at least 90% of the correct structures.
ACD/Labs has provided us with the 30 sets of 1D and 2D spectra together with the pairs of correct and incorrect structures. We are offering these up in a new 2D NMR Spectral Game for users to start to learn how to use the combined information available from both 1D H1 and 2D HSQC data for identifying the correct structure. The development of this game has required the development of a new tool for visualizing 2D NMR spectra on the web (kudos to Andrew Lang!) and requires the player to use the H1 NMR spectrum in the standard JSpecView applet together with the 2D data display to interrogate the data and decide on the most appropriate match. The 2D NMR Spectral Game can be played here. Good luck.