Prediction of acidity in acetonitrile solution with COSMO-RS

Journal of Computational Chemistry
Frank EckertMichael Diedenhofen

Abstract

The COSMO-RS method, a combination of the quantum chemical dielectric continuum solvation model COSMO with a statistical thermodynamics treatment for realistic solvation simulations, has been used for the prediction of pK(a) values in acetonitrile. For a variety of 93 organic acids, the directly calculated values of the free energies of dissociation in acetonitrile showed a very good correlation with the pK(a) values (r(2) = 0.97) in acetonitrile, corresponding to a standard deviation of 1.38 pK(a) units. Thus, we have a prediction method for acetonitrile pK(a) with the intercept and the slope as the only adjusted parameters. Furthermore, the pK(a) values of CH acids yielding large anions with delocalized charge can be predicted with a rmse of 1.12 pK(a) units using the theoretical values of slope and intercept resulting in truly ab initio pK(a) prediction. In contrast to our previous findings on aqueous acidity predictions the slope of the experimental pK(a) versus theoretical DeltaG(diss) was found to match the theoretical value 1/RT ln (10) very well. The predictivity of the presented method is general and is not restricted to certain compound classes. However, a systematic correction of -7.5 kcal mol(-1) is required for com...Continue Reading

References

Sep 15, 1988·Physical Review A: General Physics·A D Becke
Jun 15, 1986·Physical Review. B, Condensed Matter·J P Perdew
Jun 5, 2001·Organic Letters·B Kovacevic, Z B Maksic
Feb 19, 2002·Chemical Reviews·Christopher J. Cramer, Donald G. Truhlar
Jan 22, 2004·Journal of the American Chemical Society·Yao FuQing-Xiang Guo
Oct 20, 2005·Journal of Computational Chemistry·Frank Eckert, Andreas Klamt
Mar 25, 2006·The Journal of Organic Chemistry·Agnes KüttIlmar A Koppel
Sep 29, 2006·The Journal of Physical Chemistry. a·Gabriel da SilvaBogdan Z Dlugogorski
Aug 19, 2007·The Journal of Physical Chemistry. B·Haiting LuChang-Guo Zhan
Sep 1, 2007·The Journal of Physical Chemistry. a·Ao YuJin-Pei Cheng

❮ Previous
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Citations

Jan 1, 2010·Annual Review of Chemical and Biomolecular Engineering·Andreas KlamtWolfgang Arlt
Jan 23, 2016·The Journal of Organic Chemistry·Nicolas Daniel SpicciaAndrea Jane Robinson
Jan 8, 2016·ACS Applied Materials & Interfaces·Hark Jin KimMichael J Rose
Jul 1, 2015·Inorganic Chemistry·Matthew D Sampson, Clifford P Kubiak
Apr 15, 2016·Journal of the American Chemical Society·Zheng MengChuan-Feng Chen
Aug 3, 2016·Chemical Reviews·Eric S WiednerAaron M Appel
Mar 3, 2017·Journal of Chemical Theory and Computation·Assil Bouzid, Alfredo Pasquarello
Mar 30, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Christina Sondermann, Mark R Ringenberg
Apr 22, 2017·The Journal of Organic Chemistry·D Balaji ChandrasekharJih Ru Hwu
Apr 12, 2016·Chemistry : a European Journal·Sebastian TussingJan Paradies
Sep 25, 2015·Faraday Discussions·José A Castro-OsmaElisabeth Tangstad
Apr 7, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Alexander J HeyerCharles W Machan
Sep 10, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Eduardo Herappe-MejíaVojtech Jancik
Aug 23, 2018·Chemistry : a European Journal·Lydia WrobelMichael Mehring
Nov 23, 2018·Proceedings of the National Academy of Sciences of the United States of America·Bianca M Ceballos, Jenny Y Yang
Aug 18, 2010·Angewandte Chemie·Daniel HimmelIngo Krossing
Jun 30, 2019·Journal of Computational Chemistry·Andrey V Kulsha, Dmitry I Sharapa
Jul 18, 2015·Chemistry : a European Journal·José-Luis M AbboudMasaaki Mishima
Dec 20, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Vincent C-C WangLeif Hammarström
May 1, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Sofja TshepelevitshIvo Leito
Jun 3, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Lynn M MihichukKeith E Johnson
Jul 20, 2016·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Te HuMarcus Baumann
Jun 6, 2017·Physical Chemistry Chemical Physics : PCCP·Khaleel I AssafAla'a F Eftaiha
Jan 24, 2013·Chemical Communications : Chem Comm·Mintu PorelRajeev S Muthyala
May 4, 2018·International Journal of Peptide Research and Therapeutics·Karol SikoraWojciech Kamysz
Dec 9, 2020·Pharmaceuticals·Karol SikoraWojciech Kamysz
Jul 3, 2009·The Journal of Physical Chemistry. a·Ivo LeitoAndrey A Filatov
May 6, 2009·The Journal of Physical Chemistry. a·Aleksander TrummalIlmar A Koppel
Jun 8, 2021·Chemical Science·Jie HuangClaudia Turro
Oct 6, 2010·The Journal of Physical Chemistry. a·Karl KaupmeesIvo Leito
Oct 2, 2014·Inorganic Chemistry·Annabell G BonnOliver S Wenger
Nov 14, 2013·Journal of the American Chemical Society·Shelley A ClaridgePaul S Weiss

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