Computational Study on the Acidic Constants of Chiral Brønsted Acids in Dimethyl Sulfoxide
journal contribution
posted on 2014-05-16, 00:00 authored by Chen Yang, Xiao-Song Xue, Xin Li, Jin-Pei ChengThe p<i>K</i><sub>a</sub> values of a series of chiral
Brønsted acids, including <i>N</i>-triflylphosphoramides,
bis(sulfonyl)imides, bis(sulfuryl)imides, dicarboxylic acids, sulfonic
acids, and <i>N</i>-phosphinyl phosphoramides, were predicted
by using the SMD/M06-2x/6-311++G(2df,2p)//B3LYP/6-31+G(d) method in
DMSO. The results revealed that the calculated p<i>K</i><sub>a</sub> values ranged from −9.06 to 12.18 for different
types of acids. The influence of acidic strength on reactivity and
stereoselectivity was discussed using the calculated acidity data.
Given that the choice of catalyst with appropriate acidity is the
primary condition, several new catalyst candidates were designed by
calculating corresponding p<i>K</i><sub>a</sub> values of
parent acids.
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- 1. DOI - Is supplement to Computational Study on the Acidic Constants of Chiral Brønsted Acids in Dimethyl Sulfoxide
