Recent Developments of Computational Methods for p K a Prediction Based on Electronic Structure Theory with Solvation Models

Ryo Fujiki, Toru Matsui, Yasuteru Shigeta, Haruyuki Nakano and Norio Yoshida
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Ryo Fujiki: Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0052, Japan
Toru Matsui: Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Tsukuba 305-8577, Japan
Yasuteru Shigeta: Center for Computational Sciences, University of Tsukuba, Tsukuba 305-8577, Japan
Haruyuki Nakano: Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0052, Japan
Norio Yoshida: Department of Chemistry, Graduate School of Science, Kyushu University, Fukuoka 819-0052, Japan

J, 2021, vol. 4, issue 4, 1-16

Abstract: The protonation/deprotonation reaction is one of the most fundamental processes in solutions and biological systems. Compounds with dissociative functional groups change their charge states by protonation/deprotonation. This change not only significantly alters the physical properties of a compound itself, but also has a profound effect on the surrounding molecules. In this paper, we review our recent developments of the methods for predicting the K a , the equilibrium constant for protonation reactions or acid dissociation reactions. The p K a , which is a logarithm of K a , is proportional to the reaction Gibbs energy of the protonation reaction, and the reaction free energy can be determined by electronic structure calculations with solvation models. The charge of the compound changes before and after protonation; therefore, the solvent effect plays an important role in determining the reaction Gibbs energy. Here, we review two solvation models: the continuum model, and the integral equation theory of molecular liquids. Furthermore, the reaction Gibbs energy calculations for the protonation reactions require special attention to the handling of dissociated protons. An efficient method for handling the free energy of dissociated protons will also be reviewed.

Keywords: p K a; p K w; PCM; 3D-RISM; DFT; solvation (search for similar items in EconPapers)
JEL-codes: I1 I10 I12 I13 I14 I18 I19 (search for similar items in EconPapers)
Date: 2021
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