Single-centered hydrogen-bonded enhanced acidity (SHEA) acids: a new class of brønsted acids

Z Tian, A Fattahi, L Lis, SR Kass

Index: Tian, Zhixin; Fattahi, Alireza; Lis, Lev; Kass, Steven R. Journal of the American Chemical Society, 2009 , vol. 131, # 46 p. 16984 - 16988

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Citation Number: 38

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 p K a 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 ...