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.