Determination of solvation descriptors for ionic species: hydrogen bond acidity and basicity

The Journal of Organic Chemistry
M H Abraham, Yuan H Zhao

Abstract

Literature values of Gibbs energies of transfer of ions from water to other solvents have been used in conjunction with our solvation equation to obtain descriptors for univalent ions. It is suggested that descriptors used for nonelectrolytes are not adequate to describe transfers of single ions, and that two specific ionic descriptors (J(+) and J(-)) for cations and anions, respectively, are required. The ions studied include the alkali metal and tetraalkylammonium cations, halide and other anions, and the tetraphenylarsonium, tetraphenylphosphonium, and tetraphenylborate ions. It is shown that simple cations such as Na(+) act as very strong hydrogen bond acids and that the R(4)N(+) ions are only weak hydrogen bond acids. The halide anions are very strong hydrogen bond bases, as is also the acetate anion. Other anions, such as azide, cyanide, and nitrate, are again very strong hydrogen bond bases. The tetraphenylarsonium, tetraphenylphosphonium, and tetraphenylborate ions have no hydrogen bond acidity but are quite strong hydrogen bond bases. It is suggested that this is due to the basic properties of the phenyl groups.

References

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Citations

Mar 29, 2011·Journal of Chemical Information and Modeling·Andrei L LomizeHenry I Mosberg
Mar 29, 2011·Journal of Chemical Information and Modeling·Andrei L LomizeHenry I Mosberg
Sep 15, 2014·Journal of Chromatography. a·Bradley J VanMiddlesworth, Apryll M Stalcup
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Apr 22, 2016·Environmental Science & Technology·Luise HennebergerSatoshi Endo
May 5, 2017·Journal of the American Chemical Society·Sarah J PikeChristopher A Hunter
Jan 22, 2008·Journal of Chromatography. a·J R Torres-LapasióM H Abraham
Nov 7, 2017·Organic & Biomolecular Chemistry·Sarah J Pike, Christopher A Hunter
Jan 31, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Chul-Woong ChoJorg Thöming
Sep 8, 2010·Physical Chemistry Chemical Physics : PCCP·Michael H Abraham, William E Acree
Jul 31, 2019·Chemical Science·Sarah J PikeChristopher A Hunter
Jan 24, 2008·Antimicrobial Agents and Chemotherapy·Nassira MahmoudiDominique Mazier
Jun 18, 2005·Physical Chemistry Chemical Physics : PCCP·Michael H Abraham, Yuan H Zhao
Mar 5, 2021·Toxicology in Vitro : an International Journal Published in Association with BIBRA·Susana ProençaNynke I Kramer
Mar 25, 2005·The Journal of Organic Chemistry·Yuan H Zhao, Michael H Abraham
Apr 27, 2007·Journal of Chemical Information and Modeling·Laura SprungerMichael H Abraham
Jan 27, 2010·The Journal of Organic Chemistry·Michael H Abraham, William E Acree
Jul 5, 2021·The Science of the Total Environment·Jieying ZhouAnett Georgi
Jun 1, 2014·Environmental Science & Technology·Huichun ZhangRominder P S Suri
Nov 20, 2014·Environmental Science & Technology·Nastaran Jadbabaei, Huichun Zhang
Dec 6, 2017·Journal of the American Chemical Society·Zhichao LuBo Xu

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