Single-centered hydrogen-bonded enhanced acidity (SHEA) acids: A new class of Brønsted acids

Zhixin Tian, Alireza Fattahi, Lev Lis, Steven R. Kass

Research output: Contribution to journalArticlepeer-review

61 Scopus citations

Abstract

Hydrogen bonds are the dominant motif for organizing the three-dimensional structures of biomolecules such as carbohydrates, nucleic acids, and proteins, and serve as templates for proton transfer reactions. Computations, gas-phase acidity measurements, and pKa determinations in dimethyl sulfoxide on a series of polyols indicate that multiple hydrogen bonds to a single charged center lead to greatly enhanced acidities. A new class of Brønsted acids, consequently, is proposed.

Original languageEnglish (US)
Pages (from-to)16984-16988
Number of pages5
JournalJournal of the American Chemical Society
Volume131
Issue number46
DOIs
StatePublished - Nov 27 2009

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