Three Hydrogen Bond Donor Catalysts: Oxyanion Hole Mimics and Transition State Analogues

Journal Article · Wed Nov 14 04:00:00 EST 2012 · Journal of the American Chemical Society, 134(45):18534-18537

DOI:https://doi.org/10.1021/ja3085862· OSTI ID:1059186

Beletskiy, Evgeny V.; Schmidt, Jacob C.; Wang, Xue B.; Kass, Steven R.

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.

• Research Organization: Pacific Northwest National Laboratory (PNNL), Richland, WA (US), Environmental Molecular Sciences Laboratory (EMSL)
• Sponsoring Organization: USDOE
• DOE Contract Number: AC05-76RL01830
• OSTI ID: 1059186
• Report Number(s): PNNL-SA-88858; 44678; 42590; KC0301020
• Journal Information: Journal of the American Chemical Society, 134(45):18534-18537, Journal Name: Journal of the American Chemical Society, 134(45):18534-18537
• Country of Publication: United States
• Language: English

Related Subjects

Environmental Molecular Sciences Laboratory