Three hydrogen bond donor catalysts: Oxyanion hole mimics and transition state analogues

Evgeny V. Beletskiy, Jacob Schmidt, Xue Bin Wang, Steven R Kass

Research output: Contribution to journalArticle

38 Scopus citations

Abstract

Enzymes and their mimics use hydrogen bonds to catalyze chemical transformations. Small-molecule transition state analogues of oxyanion holes have been characterized by computations, gas-phase IR and photoelectron spectroscopy, and determination of their binding constants in acetonitrile. A new class of hydrogen bond catalysts is proposed (donors that can contribute three hydrogen bonds to a single functional group) and demonstrated in a Friedel-Crafts reaction. The employed catalyst was observed to react 100 times faster than its rotamer that can employ only two hydrogen bonds. The former compound also binds anions more tightly and was found to have a thermodynamic advantage.

Original languageEnglish (US)
Pages (from-to)18534-18537
Number of pages4
JournalJournal of the American Chemical Society
Volume134
Issue number45
DOIs
StatePublished - Nov 14 2012

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