10.1021/jo500158e.s001 Chen Yang Chen Yang Xiao-Song Xue Xiao-Song Xue Xin Li Xin Li Jin-Pei Cheng Jin-Pei Cheng Computational Study on the Acidic Constants of Chiral Brønsted Acids in Dimethyl Sulfoxide American Chemical Society 2014 acidity SMD chiral Br ønsted acids pKa values Chiral Br ønsted Acids Dimethyl SulfoxideThe pKa values bi catalyst DMSO 2014-05-16 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/Computational_Study_on_the_Acidic_Constants_of_Chiral_Br_nsted_Acids_in_Dimethyl_Sulfoxide/2290993 The 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.