Single-centered hydrogen-bonded enhanced acidity (SHEA) acids: a new class of Brønsted acids.
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 pK(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 Brønsted acids, consequently, is proposed.
Tian
Zhixin
Z
Department of Chemistry, University of Minnesota, Minneapolis, Minnesota 55455, USA.
Fattahi
Alireza
A
Lis
Lev
L
Kass
Steven R
SR