Proton solvation in protic and aprotic solvents

Journal of Computational Chemistry
Emanuele Rossini, Ernst-Walter Knapp

Abstract

Protonation pattern strongly affects the properties of molecular systems. To determine protonation equilibria, proton solvation free energy, which is a central quantity in solution chemistry, needs to be known. In this study, proton affinities (PAs), electrostatic energies of solvation, and pKA values were computed in protic and aprotic solvents. The proton solvation energy in acetonitrile (MeCN), methanol (MeOH), water, and dimethyl sulfoxide (DMSO) was determined from computed and measured pKA values for a specially selected set of organic compounds. pKA values were computed with high accuracy using a combination of quantum chemical and electrostatic approaches. Quantum chemical density functional theory computations were performed evaluating PA in the gas-phase. The electrostatic contributions of solvation were computed solving the Poisson equation. The computations yield proton solvation free energies with high accuracy, which are in MeCN, MeOH, water, and DMSO -255.1, -265.9, -266.3, and -266.4 kcal/mol, respectively, where the value for water is close to the consensus value of -265.9 kcal/mol. The pKA values of MeCN, MeOH, and DMSO in water correlates well with the corresponding proton solvation energies in these liquids,...Continue Reading

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Citations

Jun 17, 2016·Journal of Chemical Theory and Computation·Emanuele RossiniErnst-Walter Knapp
Mar 9, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Angela SîrbuVladimir B Arion
Nov 15, 2018·Physical Chemistry Chemical Physics : PCCP·Alhadji MalloumJeanet Conradie
Oct 1, 2019·Journal of Computational Chemistry·Alhadji MalloumJeanet Conradie
Sep 19, 2017·Biophysics Reviews·Fernando Luís Barroso daSilva, Luis Gustavo Dias
Apr 10, 2017·The Journal of Chemical Physics·Alhadji MalloumNejm-Eddine Jaidane
Jul 28, 2016·Journal of Computational Chemistry·Emanuele Rossini, Ernst-Walter Knapp
Jun 3, 2018·Journal of Molecular Modeling·Juanfeng LuChang-Guo Zhan
Sep 14, 2018·Chemical Science·Junfeng YangNaohiko Yoshikai
Oct 24, 2018·The Journal of Physical Chemistry. B·Oleksandr O Sofronov, Huib J Bakker

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