title: Computational study on the acidic constants of chiral Brønsted acids in dimethyl sulfoxide.
abstract: The pK(a) values of a series of chiral Brønsted acids, including N-triflylphosphoramides, bis(sulfonyl)imides, bis(sulfuryl)imides, dicarboxylic acids, sulfonic acids, and N-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 pKa 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 pK(a) values of parent acids.
authors.affiliation: State Key Laboratory of Elemento-Organic Chemistry, Department of Chemistry, and Collaborative Innovation Center of Chemical Science and Engineering, Nankai University , Tianjin 300071, China.
authors.forename: Chen
authors.initials: C
authors.lastname: Yang
authors.forename: Xiao-Song
authors.initials: XS
authors.lastname: Xue
authors.forename: Xin
authors.initials: X
authors.lastname: Li
authors.forename: Jin-Pei
authors.initials: JP
authors.lastname: Cheng
mesh_terms: D000143:Acids / Q000737:chemistry*; D002384:Catalysis; D039301:Computers, Molecular; D003998:Dicarboxylic Acids / Q000737:chemistry*; D004121:Dimethyl Sulfoxide / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D011789:Quantum Theory
chemical_list: D000143:Acids; D003998:Dicarboxylic Acids; D004121:Dimethyl Sulfoxide