Journal of the American Chemical Society, Vol.131, No.46, 16984-16988, 2009
Single-Centered Hydrogen-Bonded Enhanced Acidity (SHEA) Acids: A New Class of Bronsted 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 Bronsted acids, consequently, is proposed.