TY - JOUR
T1 - Single-centered hydrogen-bonded enhanced acidity (SHEA) acids
T2 - A new class of Brønsted acids
AU - Tian, Zhixin
AU - Fattahi, Alireza
AU - Lis, Lev
AU - Kass, Steven R.
PY - 2009
Y1 - 2009
N2 - 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.
AB - 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.
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U2 - 10.1021/ja9075106
DO - 10.1021/ja9075106
M3 - Article
C2 - 19919149
AN - SCOPUS:70450185933
SN - 0002-7863
VL - 131
SP - 16984
EP - 16988
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 46
ER -