Universal Solvation Model Based on Solute Electron Density. and on a Continuum Model of the Solvent Defined by

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1 S1 Supporting Information (PART II) 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 Aleksandr V. Marenich, Christopher J. Cramer,* and Donald G. Truhlar* Department of Chemistry and Supercomputing Institute, University of Minnesota, 207 Pleasant Street S.E., Minneapolis, MN Prepared for the Journal of Physical Chemistry B Revised March 27, 2009 Number of pages: 10 * Corresponding author cramer@umn.edu (C.J.C) and truhlar@umn.edu (D.G.T.)

2 S2 Contents: Table S1. Mean Signed Errors in Aqueous Solvation Free Energies, by Solute Class Table S2. Mean Signed Errors in Nonaqueous Solvation Free Energies, by Solute Class Table S3. Mean Signed Errors in Transfer Free Energies between Water and Organic Solvents, by Solute Class Table S4. Errors in Solvation and Transfer Free Energies for Neutrals, by Solvent page S3 S5 S7 S8

3 S3 Table S1. Mean Signed Errors (kcal/mol) in Aqueous Solvation Free Energies, by Solute Class a solute class N M05-2X B3LYP HF MIDI!6D 6-31G* 6-31+G** cc-pvtz 6-31G* 6-31G* H 2,NH 3,H 2 O,(H 2 O) unbranched alkanes branched alkanes cycloalkanes alkenes alkynes arenes alcohols phenols ethers aldehydes ketones carboxylic acids esters peroxides bifunctional H,C,O compounds aliphatic amines anilines aromatic N-heterocycles (1 N) aromatic N-heterocycles (2 Ns) nitriles hydrazines bifunctional H,C,N compounds amides ureas nitrohydrocarbons bifunctional H,C,N,O compounds

4 S4 Table S1. Continued solute class N M05-2X B3LYP HF MIDI!6D 6-31G* 6-31+G** cc-pvtz 6-31G* 6-31G* fluoroalkanes fluoroarenes chloroalkanes chloroalkenes chloroarenes bromoalkanes bromoalkenes bromoarenes multihalogen hydrocarbons halogenated bifunctional compounds thiols sulfides disulfides sulfur heterocycles halogenated sulfur compounds phosphorus compounds silicon compounds all neutral data a All the solvation free energies were obtained using the SMD model parameters and the IEF-PCM/Gaussian03 protocol for bulk electrostatics. N is the number of data in a given solute class.

5 S5 Table S2. Mean Signed Errors (kcal/mol) in Nonaqueous Solvation Free Energies, by Solute Class a solute class N M05-2X B3LYP HF MIDI!6D 6-31G* 6-31+G** cc-pvtz 6-31G* 6-31G* H 2, NH 3, H 2 O unbranched alkanes branched alkanes cycloalkanes alkenes alkynes arenes alcohols phenols ethers aldehydes ketones carboxylic acids esters, including lactones b peroxides bifunctional H,C,O compounds aliphatic amines anilines aromatic N-heterocycles (1 N) aromatic N-heterocycles (2 Ns) nitriles hydrazines bifunctional H,C,N compounds amides ureas lactams nitrohydrocarbons bifunctional H,C,N,O compounds

6 S6 Table S2. Continued solute class N M05-2X B3LYP HF MIDI!6D 6-31G* 6-31+G** cc-pvtz 6-31G* 6-31G* fluoroalkanes fluoroarenes chloroalkanes chloroalkenes chloroarenes bromoalkanes bromoalkenes bromoarenes multihalogen hydrocarbons halogenated bifunctional compounds thiols sulfides disulfides sulfur heterocycles sulfoxides phosphorus compounds silicon compounds all neutral data a All the solvation free energies were obtained using the SMD model parameters and the IEF-PCM/Gaussian03 protocol for bulk electrostatics. N is the number of data in a given solute class. b 5 lactones and 238 other esters

7 S7 Table S3. Mean Signed Errors (kcal/mol) in Transfer Free Energies between Water and Organic Solvents, by Solute Class a solute class N M05-2X B3LYP HF MIDI!6D 6-31G* 6-31+G** cc-pvtz 6-31G* 6-31G* lactones aromatic N-heterocycles bifunctional H,C,N compounds amides ureas lactams thymines and uracils bifunctional H,C,N,O compounds halogenated bifunctional compounds sulfur compounds phosphorus compounds silicon compounds all neutral data a All the solvation free energies were obtained using the SMD model parameters and the IEF-PCM/Gaussian03 protocol for bulk electrostatics. N is the number of data in a given solute class.

8 S8 Table S4. Errors (kcal/mol) in Solvation and Transfer Free Energies for Neutrals, by Solvent a solvent N b ε α β MSE c MUE d acetic acid acetonitrile acetophenone aniline anisole benzene benzonitrile benzyl alcohol bromobenzene bromoethane bromoform bromooctane n-butanol sec-butanol butanone butyl acetate n-butylbenzene sec-butylbenzene t-butylbenzene carbon disulfide carbon tetrachloride chlorobenzene chloroform chlorohexane m-cresol cyclohexane cyclohexanone decalin (mixture) decane decanol ,2-dibromoethane dibutyl ether o-dichlorobenzene ,2-dichloroethane diethyl ether diisopropyl ether N,N-dimethylacetamide N,N-dimethylformamide ,6-dimethylpyridine dimethyl sulfoxide dodecane ethanol ethoxybenzene

9 S9 Table S4. Continued solvent N b ε α β MSE c MUE d ethyl acetate ethylbenzene fluorobenzene fluoro-n-octane heptane heptanol hexadecane hexadecyl iodide hexane hexanol iodobenzene isobutanol isooctane isopropanol isopropylbenzene p-isopropyltoluene mesitylene methoxyethanol methylene chloride N-methylformamide methyl,2-pentanone methylpyridine nitrobenzene nitroethane nitromethane o-nitrotoluene nonane nonanol octane octanol pentadecane pentane pentanol perfluorobenzene phenyl ether propanol pyridine tetrachloroethene tetrahydrofuran tetrahydrothiophene dioxide tetralin toluene tributyl phosphate

10 S10 Table S4. Continued solvent N b ε α β MSE c MUE d triethylamine ,2,4-trimethylbenzene undecane water n/a n/a xylene (mixture) benzene/water n-butanol/water carbon tetrachloride/water chlorobenzene/water chloroform/water cyclohexane/water ,2-dibromoethane/water dibutyl ether/water ,2-dichloroethane/water diethyl ether/water ethyl acetate/water heptane/water hexane/water nitrobenzene/water octanol/water a ε is the solvent s dielectric constant; α is Abraham s hydrogen bond acidity parameter (which Abraham denotes as Σα 2 ); and β is Abraham s hydrogen bond basicity parameter (which Abraham denotes as Σβ 2 ). The SMD solvation energies were calculated at the M05-2X/6-31G* level of theory. b N is the number of neutral solute data in a given solvent. c Mean signed error d Mean unsigned error

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