We demonstrate that using a pressure corrected three-dimensional reference interaction site model one can accurately predict salting-out (Setschenow’s) constants for a wide range of organic compounds in aqueous solutions of NaCl. The approach, based on classical molecular force fields, offers an alternative to more heavily parametrized methods.
REFERENCES
1.
K. J.
Tielrooij
, N.
Garcia-Araez
, M.
Bonn
, and H. J.
Bakker
, “Cooperativity in ion hydration
,” Science
328
, 1006
–1009
(2010
).2.
Y.
Marcus
, “Effect of ions on the structure of water: Structure making and breaking
,” Chem. Rev.
109
, 1346
–1370
(2009
).3.
D. R.
Robinson
and W. P.
Jencks
, “The effect of concentrated salt solutions on the activity coefficient of acetyltetraglycine ethyl ester
,” J. Am. Chem. Soc.
87
, 2470
–2479
(1965
).4.
W. F.
McDevit
and F. A.
Long
, “The activity coefficient of benzene in aqueous salt solutions
,” J. Am. Chem. Soc.
74
, 1773
–1777
(1952
).5.
M. G.
Cacace
, E. M.
Landau
, and J. J.
Ramsden
, “The Hofmeister series: Salt and solvent effects on interfacial phenomena
,” Q. Rev. Biophys.
30
, 241
–277
(1997
).6.
J. W.
Readman
, R. F. C.
Mantoura
, and M. M.
Rhead
, “The physico-chemical speciation of polycyclic aromatic hydrocarbons (PAH) in aquatic systems
,” Z. Anal. Chem.
319
, 126
(1984
).7.
W.
Mabey
and T.
Mill
, “Critical review of hydrolysis of organic compounds in water under environmental conditions
,” J. Phys. Chem. Ref. Data
7
, 383
–415
(1978
).8.
R. A.
Park
, J. S.
Clough
, and M. C.
Wellman
, “AQUATOX: Modeling environmental fate and ecological effects in aquatic ecosystems
,” Ecol. Modell.
213
, 1
–15
(2008
).9.
B. A.
Holmberg
, H.
Wang
, J. M.
Norbeck
, and Y.
Yan
, “Controlling size and yield of zeolite y nanocrystals using tetramethylammonium bromide
,” Microporous Mesoporous Mater.
59
, 13
–28
(2003
).10.
S.
Sasaki
, S.
Koga
, R.
Imabayashi
, and H.
Maeda
, “Salt effects on the volume phase transition of ionic gel induced by the hydrophobic counterion biding
,” J. Phys. Chem. B
105
, 5852
–5855
(2001
).11.
W.
Melander
and C.
Horváth
, “Salt effects on hydrophobic interactions in precipitation and chromatography of proteins: An interpretation of the lyotropic series
,” Arch. Biochem. Biophys.
183
, 200
–215
(1977
).12.
Y. J.
Zhang
and P. S.
Cremer
, “Chemistry of Hofmeister anions and osmolytes
,” Annu. Rev. Phys. Chem.
61
, 63
–83
(2010
).13.
L.
Li
, C. J.
Fennell
, and K. A.
Dill
, “Small molecule solvation changes due to the presence of salt are governed by the cost of solvent cavity formation and dispersion
,” J. Chem. Phys.
141
, 22D518
(2014
).14.
S.
Endo
, A.
Pfennigsdorff
, and K.-U.
Goss
, “Salting-out effect in aqueous NaCl solutions: Trends with size and polarity of solute molecules
,” Environ. Sci. Technol.
46
, 1496
–1503
(2012
).15.
V.
Sergiievskyi
, G.
Jeanmairet
, M.
Levesque
, and D.
Borgis
, “Solvation free-energy pressure corrections in the three dimensional reference interaction site model
,” J. Chem. Phys.
143
, 184116
(2015
).16.
M.
Misin
, D. S.
Palmer
, and M. V.
Fedorov
, “Predicting solvation free energies using parameter-free solvent models
,” J. Phys. Chem. B
120
, 5724
(2016
).17.
M.
Misin
, M. V.
Fedorov
, and D. S.
Palmer
, “Hydration free energies of molecular ions from theory and simulation
,” J. Phys. Chem. B
120
, 975
–983
(2016
).18.
19.
Y.
Marcus
, “Individual ionic surface tension increments in aqueous solutions
,” Langmuir
29
, 2881
–2888
(2013
).20.
M. A.
Schlautman
, S.
Yim
, E. R.
Carraway
, J. H.
Lee
, and B. E.
Herbert
, “Testing a surface tension-based model to predict the salting out of polycyclic aromatic hydrocarbons in model environmental solutions
,” Water Res.
38
, 3331
–3339
(2004
).21.
W.
Li
and Y.
Mu
, “Hydration patterns and salting effects in sodium chloride solution
,” J. Chem. Phys.
135
, 134502
(2011
).22.
D.
Beglov
and B.
Roux
, “An integral equation to describe the solvation of polar molecules in liquid water
,” J. Phys. Chem.
101
, 7821
–7826
(1997
).23.
E. L.
Ratkova
, D. S.
Palmer
, and M. V.
Fedorov
, “Solvation thermodynamics of organic molecules by the molecular integral equation theory: Approaching chemical accuracy
,” Chem. Rev.
115
, 6312
–6356
(2015
).24.
F.
Hirata
, Molecular Theory of Solvation
(Kluwer Academic Publishers
, New York
, 2003
).25.
G. N.
Chuev
, S.
Chiodo
, S. E.
Erofeeva
, M. V.
Fedorov
, N.
Russo
, and E.
Sicilia
, “A quasilinear RISM approach for the computation of solvation free energy of ionic species
,” Chem. Phys. Lett.
418
, 485
–489
(2006
).26.
M.
Misin
, M. V.
Fedorov
, and D. S.
Palmer
, “Communication: Accurate hydration free energies at a wide range of temperatures from 3D-RISM
,” J. Chem. Phys.
142
, 091105
(2015
).27.
B.
Li
, A. V.
Matveev
, and N.
Rösch
, “Three-dimensional reference interaction site model solvent combined with a quantum mechanical treatment of the solute
,” Comput. Theor. Chem.
1070
, 143
–151
(2015
).28.
J.
Johnson
, D. A.
Case
, T.
Yamazaki
, S.
Gusarov
, A.
Kovalenko
, and T.
Luchko
, “Small molecule hydration energy and entropy from 3D-RISM
,” J. Phys.: Condens. Matter
28
, 344002
(2016
).29.
T.
Sumi
, A.
Mitsutake
, and Y.
Maruyama
, “A solvation-free-energy functional: A reference-modified density functional formulation
,” J. Comput. Chem.
36
, 1359
–1369
(2015
).30.
G.
Jeanmairet
, M.
Levesque
, V.
Sergiievskyi
, and D.
Borgis
, “Molecular density functional theory for water with liquid-gas coexistence and correct pressure
,” J. Chem. Phys.
142
, 154112
(2015
).31.
Y.
Ebato
and T.
Miyata
, “A pressure consistent bridge correction of kovalenko-hirata closure in ornstein-zernike theory for lennard-jones fluids by apparently adjusting sigma parameter
,” AIP Adv.
6
, 055111
(2016
).32.
F.
Mrugalla
and S. M.
Kast
, “Designing molecular complexes using free-energy derivatives from liquid-state integral equation theory
,” J. Phys.: Condens. Matter
28
, 344004
(2016
).33.
T.
Hayashi
, H.
Oshima
, Y.
Harano
, and M.
Kinoshita
, “Water based on a molecular model behaves like a hard-sphere solvent for a nonpolar solute when the reference interaction site model and related theories are employed
,” J. Phys.: Condens. Matter
28
, 344003
(2016
).34.
M.
Kinoshita
and F.
Hirata
, “Analysis of salt effects on solubility of noble gases in water using the reference interaction site model theory
,” J. Chem. Phys.
106
, 5202
–5215
(1997
).35.
T.
Imai
, M.
Kinoshita
, and F.
Hirata
, “Salt effect on stability and solvation structure of peptide: An integral equation study
,” Bull. Chem. Soc. Jpn.
73
, 1113
–1122
(2000
).36.
R.
Ishizuka
, G. A.
Huber
, and J. A.
McCammon
, “Solvation effect on the conformations of alanine dipeptide: Integral equation approach
,” J. Phys. Chem. Lett.
1
, 2279
–2283
(2010
).37.
Y.
Maruyama
, N.
Yoshida
, and F.
Hirata
, “Electrolytes in biomolecular systems studied with the 3D-RISM/RISM theory
,” Interdiscip. Sci.: Comput. Life Sci.
3
, 290
–307
(2011
).38.
F.
Moučka
, I.
Nezbeda
, and W. R.
Smith
, “Molecular force fields for aqueous electrolytes: SPC/E-compatible charged LJ sphere models and their limitations
,” J. Chem. Phys.
138
, 154102
(2013
).39.
B.
Hess
, C.
Holm
, and N. v. d.
Vegt
, “Osmotic coefficients of atomistic NaCl (aq) force fields
,” J. Chem. Phys.
124
, 164509
(2006
).40.
M.
Patra
and M.
Karttunen
, “Systematic comparison of force fields for microscopic simulations of NaCl in aqueous solutions: Diffusion, free energy of hydration, and structural properties
,” J. Comput. Chem.
25
, 678
–689
(2004
).41.
A.
Asmadi
, T.
Kirchner
, W.
Abdallah
, M. V.
Fedorov
, and M. R.
Stukan
, “Influence of the drude charge value on the performance of polarisable water model: A test for microscopic and macroscopic parameters
,” J. Mol. Liq.
188
, 245
–251
(2013
).42.
H. J. C.
Berendsen
, J. R.
Grigera
, and T. P.
Straatsma
, “The missing term in effective pair potentials
,” J. Phys. Chem.
91
, 6269
–6271
(1987
).43.
Computer Simulation of Liquids
, edited by M. P.
Allen
and D. J.
Tildesley
(Clarendon Press
, Oxford, UK
, 1987
).44.
L. X.
Dang
, “Mechanism and thermodynamics of ion selectivity in aqueous solutions of 18-crown-6 ether: A molecular dynamics study
,” J. Am. Chem. Soc.
117
, 6954
–6960
(1995
).45.
I. S.
Joung
and T. E.
Cheatham
, “Determination of alkali and halide monovalent ion parameters for use in explicitly solvated biomolecular simulations
,” J. Phys. Chem. B
112
, 9020
–9041
(2008
).46.
S.
Deublein
, J.
Vrabec
, and H.
Hasse
, “A set of molecular models for alkali and halide ions in aqueous solution
,” J. Chem. Phys.
136
, 084501
(2012
).47.
D.
Horinek
, S. I.
Mamatkulov
, and R. R.
Netz
, “Rational design of ion force fields based on thermodynamic solvation properties
,” J. Chem. Phys.
130
, 124507
(2009
).48.
N. M.
O’Boyle
, M.
Banck
, C. A.
James
, C.
Morley
, T.
Vandermeersch
, and G. R.
Hutchison
, “Open babel: An open chemical toolbox
,” J. Cheminf.
3
, 33
(2011
).49.
N. M.
O’Boyle
, C.
Morley
, and G. R.
Hutchison
, “Pybel: A python wrapper for the OpenBabel cheminformatics toolkit
,” Chem. Cent. J.
2
, 1
–5
(2008
).50.
Y.
Zhao
and D. G.
Truhlar
, “The m06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: Two new functionals and systematic testing of four m06-class functionals and 12 other functionals
,” Theor. Chem. Acc.
120
, 215
–241
(2007
).51.
B. J.
Lynch
, Y.
Zhao
, and D. G.
Truhlar
, “Effectiveness of diffuse basis functions for calculating relative energies by density functional theory
,” J. Phys. Chem. A
107
, 1384
–1388
(2003
).52.
M. J.
Frisch
, G. W.
Trucks
, H. B.
Schlegel
, G. E.
Scuseria
, M. A.
Robb
, J. R.
Cheeseman
, G.
Scalmani
, V.
Barone
, B.
Mennucci
, G. A.
Petersson
, H.
Nakatsuji
, M.
Caricato
, X.
Li
, H. P.
Hratchian
, A. F.
Izmaylov
, J.
Bloino
, G.
Zheng
, J. L.
Sonnenberg
, M.
Hada
, M.
Ehara
, K.
Toyota
, R.
Fukuda
, J.
Hasegawa
, M.
Ishida
, T.
Nakajima
, Y.
Honda
, O.
Kitao
, H.
Nakai
, T.
Vreven
, J. A.
Montgomery
, Jr., J. E.
Peralta
, F.
Ogliaro
, M.
Bearpark
, J. J.
Heyd
, E.
Brothers
, K. N.
Kudin
, V. N.
Staroverov
, R.
Kobayashi
, J.
Normand
, K.
Raghavachari
, A.
Rendell
, J. C.
Burant
, S. S.
Iyengar
, J.
Tomasi
, M.
Cossi
, N.
Rega
, J. M.
Millam
, M.
Klene
, J. E.
Knox
, J. B.
Cross
, V.
Bakken
, C.
Adamo
, J.
Jaramillo
, R.
Gomperts
, R. E.
Stratmann
, O.
Yazyev
, A. J.
Austin
, R.
Cammi
, C.
Pomelli
, J. W.
Ochterski
, R. L.
Martin
, K.
Morokuma
, V. G.
Zakrzewski
, G. A.
Voth
, P.
Salvador
, J. J.
Dannenberg
, S.
Dapprich
, A. D.
Daniels
, Ö.
Farkas
, J. B.
Foresman
, J. V.
Ortiz
, J.
Cioslowski
, and D. J.
Fox
, gaussian 09, Revision D.01, Gaussian, Inc., Wallingford, CT, 2009.53.
A. V.
Marenich
, C. J.
Cramer
, and D. G.
Truhlar
, “Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions
,” J. Phys. Chem. B
113
, 6378
–6396
(2009
).54.
J. L.
Banks
, H. S.
Beard
, Y.
Cao
, A. E.
Cho
, W.
Damm
, R.
Farid
, A. K.
Felts
, T. A.
Halgren
, D. T.
Mainz
, J. R.
Maple
, R.
Murphy
, D. M.
Philipp
, M. P.
Repasky
, L. Y.
Zhang
, B. J.
Berne
, R. A.
Friesner
, E.
Gallicchio
, and R. M.
Levy
, “Integrated modeling program, applied chemical theory (IMPACT)
,” J. Comput. Chem.
26
, 1752
–1780
(2005
).55.
Maestro
(Schrödinger, LLC
, New York
, 2014
).56.
A. V.
Marenich
, S. V.
Jerome
, C. J.
Cramer
, and D. G.
Truhlar
, “Charge model 5: An extension of hirshfeld population analysis for the accurate description of molecular interactions in gaseous and condensed phases
,” J. Chem. Theory Comput.
8
, 527
–541
(2012
).57.
A.
Marenich
, C.
Cramer
, and D.
Truhlar
, CM5PAC
(University of Minnesota
, Minneapolis, MN
, 2013
).58.
J.
Perkyns
and B. M.
Pettitt
, “A site–site theory for finite concentration saline solutions
,” J. Chem. Phys.
97
, 7656
–7666
(1992
).59.
P.
Novotny
and O.
Sohnel
, “Densities of binary aqueous solutions of 306 inorganic substances
,” J. Chem. Eng. Data
33
, 49
–55
(1988
).60.
S. M.
Kast
and T.
Kloss
, “Closed-form expressions of the chemical potential for integral equation closures with certain bridge functions
,” J. Chem. Phys.
129
, 236101
(2008
).61.
T.
Luchko
, S.
Gusarov
, D. R.
Roe
, C.
Simmerling
, D. A.
Case
, J.
Tuszynski
, and A.
Kovalenko
, “Three-dmensional molecular theory of solvation coupled with molecular dynamics in amber
,” J. Chem. Theory Comput.
6
, 607
–624
(2010
).62.
A.
Kovalenko
and F.
Hirata
, “Potentials of mean force of simple ions in ambient aqueous solution. I. Three-dimensional reference interaction site model approach
,” J. Chem. Phys
112
, 10391
–10402
(2000
).63.
A.
Kovalenko
and F.
Hirata
, “Self-consistent description of a metal-water interface by the kohn-sham density functional theory and the three-dimensional reference interaction site model
,” J. Chem. Phys.
110
, 10095
–10112
(1999
).64.
M.
Lund
, L.
Vrbka
, and P.
Jungwirth
, “Specific ion binding to nonpolar surface patches of proteins
,” J. Am. Chem. Soc.
130
, 11582
–11583
(2008
).65.
P. E.
Smith
, “Computer simulation of cosolvent effects on hydrophobic hydration
,” J. Phys. Chem. B
103
, 525
–534
(1999
).66.
P.
Jungwirth
and D. J.
Tobias
, “Surface effects on aqueous ionic solvation: A molecular dynamics simulation study of NaCl at the air/water interface from infinite dilution to saturation
,” J. Phys. Chem. B
104
, 7702
–7706
(2000
).67.
P. B.
Petersen
and R. J.
Saykally
, “On the nature of ions at the liquid water surface
,” Annu. Rev. Phys. Chem.
57
, 333
–364
(2006
).68.
M. V.
Fedorov
and A. A.
Kornyshev
, “Unravelling the solvent response to neutral and charged solutes
,” Mol. Phys.
105
, 1
–16
(2007
).69.
Y.
Levin
, “Electrostatic correlations: From plasma to biology
,” Rep. Prog. Phys.
65
, 1577
(2002
).70.
M. V.
Fedorov
and A. A.
Kornyshev
, “Ionic liquids at electrified interfaces
,” Chem. Rev.
114
, 2978
–3036
(2014
).71.
A.
Klamt
, COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design
(Elsevier Science
, Amsterdam
, 2005
).72.
N.
Ni
and S. H.
Yalkowsky
, “Prediction of Setschenow constants
,” Int. J. Pharm.
254
, 167
–172
(2003
).73.
Y.
Li
, Q.
Hu
, and C.
Zhong
, “Topological modeling of the Setschenow constant
,” Ind. Eng. Chem. Res.
43
, 4465
–4468
(2004
).74.
J.
Xu
, L.
Wang
, L.
Wang
, X.
Shen
, and W.
Xu
, “QSPR study of Setschenow constants of organic compounds using MLR, ANN, and SVM analyses
,” J. Comput. Chem.
32
, 3241
–3252
(2011
).75.
X.
Yu
and R.
Yu
, “Setschenow constant prediction based on the IEF-PCM calculations
,” Ind. Eng. Chem. Res.
52
, 11182
–11188
(2013
).76.
F.
Archambault
, C.
Chipot
, I.
Soteras
, F. J.
Luque
, K.
Schulten
, and F.
Dehez
, “Polarizable intermolecular potentials for water and benzene interacting with halide and metal ions
,” J. Chem. Theory Comput.
5
, 3022
–3031
(2009
).77.
W.
Kunz
et al, “Osmotic coefficients and surface tensions of aqueous electrolyte solutions: Role of dispersion forces
,” J. Phys. Chem. B
108
, 2398
–2404
(2004
).© 2016 Author(s).
2016
Author(s)
You do not currently have access to this content.
