Bond Motions Reveal Reaction Outcomes

Researchers have developed a mathematical method for using information about molecular bond motions to help predict the stereoselective outcome of catalytic reactions (Nature 2014, DOI: 10.1038/nature13019). Such a generalizable tool, coupledwith information about molecular sterics and electronics, could enable scientists to more precisely tailor their designs and syntheses of drugs and materials, say the study’s authors, Matthew S. Sigman, Anat Milo, and Elizabeth N. Bess of the University of Utah. The authors were able to correlate the way bonds vibrate in response to infrared radiation with reaction outcomes in a number of cases. On the basis of these correlations, they then devised a computational model that could be used to predict the outcomes of other reactions. They tested the method with three reaction classes: the peptide-catalyzed reaction of bisphenols with acetic anhydride, the enantioselective hydrogenation of 1,1-di­arylalkene, and the oxidative Heck reaction. The group performed the reactions in the lab and found that the results validated the model.