Enzymes and their mimics use hydrogen bonds to catalyze chemical transformations. Small molecule transition state analogs of oxyanion holes are characterized by gas phase IR and photoelectron spectroscopy and their binding constants in acetonitrile. As a result, a new class of hydrogen bond catalysts is proposed (OH donors that can contribute three hydrogen bonds to a single functional group) and demonstrated in a Friedel-Crafts reaction.
Revised: September 11, 2013 |
Published: November 14, 2012
Citation
Beletskiy E.V., J.C. Schmidt, X.B. Wang, and S.R. Kass. 2012.Three Hydrogen Bond Donor Catalysts: Oxyanion Hole Mimics and Transition State Analogues.Journal of the American Chemical Society 134, no. 45:18534-18537.PNNL-SA-88858.doi:10.1021/ja3085862