Tables From Review Article
Data Tables From Review Article
Table 5. Calculated and experimental free energies of
solvation for neutral solutes used in the parameterization of SM2 and SM3
(kcal/mol)
A = 
B = 
C = 
SM1a SM2 SM3 Expt
Compound A B C A B C A B C C
hydrocarbons
ethane 0.0 0.8 0.8 0.0 1.2 1.2 0.0 1.2 1.2 1.8
propane 0.0 1.0 1.0 0.0 1.4 1.4 0.0 1.4 1.4 2.0
cyclopropane -0.2 0.9 0.7 -0.1 1.3 1.1 -0.2 1.3 1.1 0.8
butane 0.1 1.1 1.2 0.1 1.6 1.7 0.0 1.6 1.7 2.1
2-methylpropane 0.1 1.0 1.1 0.1 1.6 1.6 0.0 1.6 1.7 2.3
neopentane 0.1 1.2 1.3 0.1 1.7 1.9 0.1 1.8 1.8 2.5
cyclopentane 0.0 1.0 1.0 0.1 1.5 1.6 0.0 1.6 1.6 1.2
hexane 0.2 1.3 1.5 0.2 2.0 2.2 0.1 2.1 2.1 2.5
cyclohexane 0.2 1.2 1.4 0.2 1.7 1.9 0.1 1.8 1.8 1.2
heptane 0.2 1.4 1.6 0.2 2.2 2.5 0.1 2.2 2.4 2.6
2,4-dimethylpentane 0.3 1.3 1.6 0.3 2.1 2.4 0.1 2.2 2.3 2.9
methylcyclohexane 0.3 1.2 1.5 0.3 1.9 2.1 0.1 2.0 2.1 1.7
octane 0.3 1.6 1.9 0.3 2.4 2.7 0.1 2.5 2.6 2.9
cis-1,2-dimethylcyclohexane 0.3 1.3 1.6 0.3 2.0 2.4 0.2 2.1 2.3 1.6
ethene -0.3 0.7 0.4 -0.3 1.1 0.8 -0.3 1.2 0.9 1.3
2-methylpropene -0.4 1.0 0.6 -0.4 1.5 1.1 -0.4 1.6 1.2 1.2
propene -0.3 0.8 0.5 -0.3 1.3 1.0 -0.3 1.4 1.1 1.3
E-2-pentene -0.3 1.2 0.9 -0.3 1.7 1.4 -0.3 1.8 1.5 1.3
cyclopentene -0.5 1.1 0.6 -0.4 1.5 1.0 -0.6 1.6 1.1 0.6
1,3-butadiene -0.9 0.8 -0.1 -0.9 1.4 0.6 -2.4 1.6 -0.8 0.6
benzene -1.9 0.9 -1.0 -2.0 1.4 -0.5 -2.0 1.7 -0.3 -0.9
toluene -1.9 1.1 -0.8 -1.9 1.7 -0.3 -2.0 1.9 -0.1 -0.9
o-xylene -1.9 1.2 -0.7 -2.0 1.8 -0.1 -2.0 2.1 0.1 -0.9
m-xylene -1.9 1.2 -0.7 -1.9 1.9 0.0 -1.9 2.1 0.2 -0.8
p-xylene -1.8 1.0 -0.8 -1.9 1.9 0.0 -1.9 2.1 0.2 -0.8
naphthalene -3.5 1.2 -2.3 -3.5 1.8 -1.8 -3.8 2.2 -1.5 -2.4
anthracene -4.9 1.6 -3.3 -4.8 2.2 -2.5 -5.0 2.8 -2.2 -4.2
ethyne -1.8 0.6 -1.2 -1.8 1.0 -0.9 -2.3 1.2 -1.2 0.0
propyne -2.1 1.0 -1.1 -2.1 1.2 -0.9 -2.5 1.4 -1.1 -0.3
1-butyne -1.9 0.9 -1.0 -1.9 1.4 -0.5 -2.4 1.6 -0.8 -0.2
1-pentyne -1.8 1.1 -0.7 -1.8 1.6 -0.2 -2.3 1.8 -0.5 0.0
1-hexyne -1.8 1.1 -0.6 -1.8 1.8 0.0 -2.4 2.1 -0.3 0.3
butenyne -2.5 0.8 -1.7 -2.5 1.3 -1.2 -3.0 1.6 -1.4 0.0
Mean unsigned error 0.5 0.7
H, C, N compounds
ethylamine -1.3 -3.2 -4.5 -1.3 -3.9 -5.2 -0.1 -5.4 -5.5 -4.5
1-propylamine -1.3 -3.7 -5.0 -1.3 -3.7 -5.0 -0.1 -5.2 -5.3 -4.4
1-butanamine -1.2 -3.2 -4.4 -1.2 -3.5 -4.7 0.0 -5.0 -5.0 -4.3
aniline -2.5 -2.3 -4.8 -2.6 -3.2 -5.8 -2.3 -4.4 -6.7 -4.9
dimethylamine -2.5 -1.9 -4.4 -2.6 -1.8 -4.3 -0.3 -2.7 -3.0 -4.3
pyrrolidine -2.0 -1.8 -3.8 -1.8 -1.7 -3.4 -0.1 -2.5 -2.6 -5.5
piperazine -3.6 -4.0 -7.6 -3.7 -4.1 -7.8 -0.5 -5.7 -6.1 -7.4
trimethylamine -3.3 -1.6 -4.9 -3.3 0.7 -2.6 -0.6 0.5 -0.2 -3.2
pyridine -3.9 -0.4 -4.3 -3.9 -0.5 -4.4 -3.0 -0.9 -3.9 -4.7
2-methylpyrazine -4.8 -1.2 -6.0 -4.8 -1.9 -6.7 -3.3 -2.8 -6.1 -5.5
acetonitrile -2.1 -2.2 -4.3 -2.0 -2.4 -4.3 -2.8 -3.4 -6.2 -3.9
propanenitrile -1.8 -2.1 -3.9 -1.8 -2.0 -3.8 -2.4 -3.0 -5.4 -3.9
butanenitrile -1.6 -1.9 -3.5 -1.6 -1.8 -3.4 -2.2 -2.8 -4.9 -3.7
N-methylpiperazine -4.4 -2.5 -6.9 -4.4 -1.7 -6.2 -0.8 -2.7 -3.5 -7.8
N,N'-dimethylpiperazine -5.3 -2.0 -7.3 -5.3 0.6 -4.6 -0.9 0.3 -0.6 -7.6
4-methylpyridine -4.0 -0.2 -4.2 -3.9 -0.3 -4.2 -3.1 -0.7 -3.7 -4.9
azetidine -1.5 -3.5 -5.0 -1.6 -2.1 -3.7 -0.4 -3.1 -3.4 -5.6
2,6-dimethylpyridine -2.8 0.4 -2.4 -2.8 0.5 -2.3 -2.4 0.3 -2.1 -4.6
Mean unsigned error 0.6 1.0 2.0
H, C, O compounds
methanol -1.0 -4.4 -5.4 -1.0 -4.7 -5.8 -1.0 -4.3 -5.3 -5.1
ethanol -1.0 -3.4 -4.4 -1.0 -3.9 -4.9 -1.1 -3.5 -4.6 -5.0
dimethyl ether -1.2 -1.5 -2.7 -1.1 -0.4 -1.4 -0.8 -0.6 -1.4 -1.9
acetaldehyde -3.1 -0.7 -3.8 -3.0 -1.5 -4.5 -3.3 -2.0 -5.2 -3.5
acetic acid -2.3 -4.8 -7.1 -2.1 -5.6 -7.7 -2.7 -5.8 -8.5 -6.7
methyl formate -2.4 -2.8 -5.2 -2.4 -2.4 -4.8 -3.3 -3.2 -6.5 -2.8
1,2-ethanediol -1.6 -7.0 -8.6 -1.6 -8.1 -9.6 -1.7 -7.4 -9.1 -7.7
1-propanol -0.9 -3.2 -4.1 -0.9 -3.7 -4.6 -1.0 -3.3 -4.3 -4.8
i-propanol -0.9 -2.9 -3.8 -0.9 -3.2 -4.1 -0.8 -2.9 -3.6 -4.8
prop-2-en-1-ol -1.3 -3.5 -4.8 -1.2 -3.7 -4.9 -0.4 -3.2 -3.6 -5.0
2-methoxyethanol -1.4 -5.3 -6.7 -1.4 -4.9 -6.3 -1.5 -4.7 -6.2 -6.8
propanal -2.6 -0.5 -3.1 -2.6 -1.0 -3.6 -3.0 -1.4 -4.5 -3.5
propanone -3.3 -0.4 -3.7 -3.2 -1.0 -4.1 -3.3 -1.5 -4.7 -3.9
propanoic acid -1.6 -4.4 -6.0 -1.6 -5.1 -6.7 -2.2 -5.2 -7.4 -6.5
methyl acetate -2.3 -2.0 -4.3 -2.3 -1.7 -4.0 -2.3 -2.4 -4.7 -3.3
t-butanol -0.8 -2.3 -3.1 -0.9 -2.4 -3.3 -0.7 -2.1 -2.8 -4.5
diethyl ether -0.9 0.2 -0.7 -0.9 0.7 -0.2 -0.7 0.6 -0.2 -1.6
1-methoxypropane -0.9 -0.8 -1.7 -0.9 0.4 -0.5 -0.7 0.2 -0.5 -1.7
2-methoxypropane -0.9 -0.6 -1.5 -0.9 0.5 -0.4 -0.7 0.3 -0.4 -2.0
1,2-dimethoxyethane -1.7 -2.5 -4.2 -1.7 -0.8 -2.5 -1.2 -1.2 -2.5 -4.8
butanal -2.5 -0.3 -2.8 -2.5 -0.8 -3.3 -2.9 -1.2 -4.1 -3.2
butanone -2.8 -0.1 -2.9 -2.8 -0.5 -3.2 -3.1 -0.9 -4.0 -3.6
butanoic acid -1.5 -4.2 -5.7 -1.5 -4.9 -6.3 -2.0 -5.0 -7.0 -6.4
ethyl acetate -2.2 -1.1 -3.3 -2.2 -1.2 -3.3 -2.2 -1.8 -4.0 -3.1
methyl propanoate -1.8 -1.5 -3.3 -1.8 -1.2 -3.0 -1.8 -1.9 -3.7 -2.9
2-methoxy-2-methylpropane -0.8 -0.2 -1.0 -0.8 0.8 0.0 -0.6 0.6 0.0 -2.2
2-pentanone -2.3 0.2 -2.1 -2.3 0.0 -2.3 -2.6 -0.4 -3.1 -3.5
3-pentanone -2.4 0.2 -2.2 -2.4 0.0 -2.4 -2.8 -0.3 -3.1 -3.4
methyl butanoate -1.7 -1.4 -3.1 -1.7 -1.0 -2.7 -1.6 -1.7 -3.3 -2.8
4-heptanone -2.1 0.5 -1.6 -2.0 0.4 -1.6 -2.4 0.1 -2.3 -2.9
5-nonanone -2.2 0.7 -1.5 -2.2 0.8 -1.4 -2.5 0.5 -2.0 -2.7
tetrahydrofuran -1.4 -1.7 -3.1 -1.4 -0.2 -1.5 -1.2 -0.4 -1.7 -3.5
1,4-dioxane -2.0 -3.9 -5.9 -2.0 -1.4 -3.4 -1.5 -2.0 -3.5 -5.1
phenol -2.5 -3.3 -5.8 -2.5 -3.3 -5.8 -2.7 -2.7 -5.4 -6.6
benzaldehyde -4.1 -0.3 -4.4 -4.1 -0.7 -4.7 -4.6 -0.9 -5.5 -4.0
acetophenone -4.3 -0.1 -4.4 -4.3 -0.1 -4.4 -4.7 -0.4 -5.1 -4.6
m-hydroxybenzaldehyde -4.2 -4.5 -8.7 -4.2 -5.4 -9.5 -5.2 -5.3 -10.6 -9.5
p-hydroxybenzaldehyde -4.4 -4.6 -9.0 -4.4 -5.3 -9.8 -5.5 -5.3 -10.8 -10.5
Mean unsigned error 0.7 0.8 1.1
H, C, F compounds
fluoromethane -1.4 1.6 0.2 -1.4 1.8 0.4 -0.9 1.7 0.8 -0.2
trifluoromethane -3.1 3.1 0.0 -3.2 3.2 0.1 -3.3 2.9 -0.4 0.8
tetrafluoromethane -0.6 4.1 3.5 -0.6 4.0 3.4 -0.4 3.5 3.1 3.1
1,1-difluoroethane -2.3 2.3 -0.0 -2.4 2.6 0.3 -1.8 2.5 0.6 -0.1
Mean unsigned error 0.4 0.5 0.7
H, P compound
phosphine 0.0 0.6 0.6 0.0 0.6 0.6 -1.0 1.6 0.6 0.6
Unsigned error 0.0 0.0 0.0
H, C, S compounds
methanethiol -0.2 -0.8 -1.0 -0.2 -0.7 -0.8 -0.2 -0.7 -0.9 -1.2
ethanethiol -0.3 -0.3 -0.6 -0.3 -0.3 -0.6 -0.4 -0.3 -0.7 -1.3
dimethyl sulfide -0.1 -1.4 -1.5 -0.1 -1.5 -1.6 -0.5 -1.6 -2.1 -1.4
diethyl sulfide -0.1 -0.3 -0.4 -0.1 -0.3 -0.4 -1.0 -0.4 -1.4 -1.3
thiophenol -3.2 -0.7 -3.9 -3.2 0.0 -3.2 -2.8 0.2 -2.5 -2.6
thiosnisole -3.5 -0.6 -4.1 -3.5 -0.7 -4.2 -3.0 -0.5 -3.5 -2.7
Mean unsigned error 0.8 0.7 0.4
H, C, Cl compounds
methyl chloride -1.0 0.2 -0.8 -1.0 0.3 -0.7 -0.4 0.2 -0.2 -0.6
dichloromethane -1.0 -0.2 -1.2 -1.0 -0.2 -1.2 -0.3 -0.3 -0.7 -1.4
chloroform -0.7 -0.5 -1.2 -0.7 -0.5 -1.2 -0.2 -0.7 -0.9 -1.1
ethyl chloride -1.0 0.2 -0.8 -1.0 0.6 -0.5 -0.6 0.5 -0.1 -0.6
1,2-dichloroethane -0.9 -0.1 -1.0 -1.0 -0.1 -1.0 -0.5 -0.2 -0.7 -1.7
1,1,1-trichloroethane -1.0 -0.1 -1.1 -0.9 -0.1 -1.0 -0.3 -0.3 -0.6 -0.3
1,1,2-trichloroethane -1.0 -0.3 -1.3 -1.1 -0.3 -1.4 -0.4 -0.5 -0.9 -2.0
isopropyl chloride -1.1 0.6 -0.5 -1.1 0.8 -0.3 -0.6 0.8 0.2 -0.3
vinyl chloride -0.8 0.3 -0.5 -0.8 0.5 -0.3 -0.5 0.5 0.0 -0.6
Z-1,2,-dichloroethene -1.1 -0.1 -1.1 -1.1 0.0 -1.1 -0.7 -0.1 -0.8 -1.2
E-1,2-dichloroethene -0.5 -0.2 -0.7 -0.5 -0.2 -0.7 -0.6 -0.3 -0.9 -0.8
trichloroethene -0.6 -0.4 -1.0 -0.6 -0.4 -1.0 -1.1 -0.6 -1.7 -0.4
tetrachloroethene -0.3 -0.6 -0.9 -0.3 -0.7 -0.9 -1.8 -0.9 -2.7 0.1
chlorobenzene -2.0 0.6 -1.4 -2.0 0.9 -1.1 -2.4 1.0 -1.3 -1.1
Mean unsigned error 0.4 0.3 0.7
H, C, Br compounds
bromomethane -0.3 -0.4 -0.7 -0.4 -0.3 -0.7 -1.2 0.1 -1.1 -0.8
bromoethane -0.4 -0.2 -0.6 -0.4 0.0 -0.4 -1.6 0.4 -1.2 -0.7
2-bromopropane -0.5 0.1 -0.4 -0.5 0.3 -0.2 -1.8 0.7 -1.1 -0.5
bromobenzene -2.3 0.1 -2.2 -2.3 0.4 -2.0 -2.4 0.9 -1.5 -1.5
dibromomethane -0.2 -1.3 -1.5 -0.2 -1.3 -1.5 -1.0 -0.5 -1.5 -2.1
1,2-dibromoethane -0.6 -0.8 -1.4 -0.6 -0.9 -1.5 -2.5 -0.3 -2.8 -2.1
p-dibromobenzene -2.4 -0.8 -3.2 -2.4 -0.7 -3.2 -2.5 0.1 -2.3 -2.3
bromoform -0.2 -1.9 -2.1 -0.2 -2.0 -2.2 -0.6 -0.9 -1.5 -2.1
Mean unsigned error 0.4 0.4 0.4
H, C, I compounds
iodomethane -0.1 -0.9 -1.0 -0.1 -1.0 -1.1 -1.0 0.3 -0.7 -0.9
iodoethane 0.0 -0.7 -0.7 0.0 -0.7 -0.7 -1.6 0.6 -0.9 -0.7
1-iodopropane 0.0 -0.5 -0.5 0.0 -0.5 -0.5 -1.2 0.8 -0.4 -0.6
2-iodopropane 0.0 -0.4 -0.4 0.0 -0.4 -0.4 -1.8 0.9 -0.9 -0.5
1-iodobutane 0.1 -0.4 -0.3 0.1 -0.3 -0.2 -1.2 1.0 -0.1 -0.3
Mean unsigned error 0.1 0.1 0.2
compounds with 4 or more kinds of atoms
2-methoxyethanamine -2.2 -5.3 -7.5 -2.2 -4.9 -7.1 -0.8 -6.6 -7.4 -6.6
nitroethane -1.8 -1.9 -3.7 -1.7 -2.6 -4.4 1.3 -3.9 -2.6 -3.7
1-nitropropane -1.5 -1.8 -3.3 -1.4 -2.4 -3.8 1.3 -3.7 -2.4 -3.3
2-nitropropane -1.9 -1.6 -3.5 -1.9 -2.2 -4.1 2.0 -3.4 -1.4 -3.1
nitrobenzene -3.2 -1.6 -4.8 -3.2 -2.1 -5.2 -1.1 -3.1 -4.1 -4.1
2-methyl-1-nitrobenzene -3.5 -1.2 -4.7 -3.4 -1.6 -5.0 -1.1 -2.5 -3.6 -3.6
2,2,2-trifluoroethanol -3.2 -0.9 -4.1 -3.2 -1.4 -4.5 -3.7 -1.3 -4.9 -4.3
1,1,1-trifluoropropan-2-ol -2.3 -1.1 -3.4 -2.4 -0.8 -3.2 -2.5 -0.8 -3.3 -4.2
chlorofluoromethane -1.8 1.1 -0.7 -1.8 1.1 -0.7 -1.1 0.9 -0.2 -0.8
chlorodifluoromethane -2.1 1.8 -0.3 -2.1 1.7 -0.4 -1.7 1.5 -0.2 -0.5
2-chloro-1,1,1-trifluoroethane -2.2 2.6 0.4 -2.2 2.6 0.5 -2.0 2.2 0.2 0.1
bis-2-chloroethyl sulfide -1.6 -0.9 -2.5 -1.6 -1.6 -3.2 -0.9 -1.9 -2.8 -3.9
p-bromophenol -2.6 -4.3 -6.9 -2.7 -4.4 -7.0 -3.1 -3.5 -6.5 -7.1
bromotrifluoromethane -1.5 2.1 0.6 -1.4 1.9 0.5 -0.6 1.9 1.3 1.8
2-bromo-1-chloroethane -0.7 -0.5 -1.2 -0.7 -0.6 -1.3 -1.0 -0.3 -1.4 -2.0
3-ethyl-2-methoxypyrazine -4.6 -0.9 -5.5 -4.3 -1.5 -5.8 -3.2 -2.4 -5.6 -4.4
morpholine -2.8 -4.0 -6.8 -2.9 -2.7 -5.6 -1.1 -3.9 -4.9 -7.2
P(OCH3)3 -6.0 -3.3 -9.2 -5.9 -0.8 -6.7 -6.3 -0.9 -7.2 -8.7
P(OC2H5)3 -5.2 -1.0 -6.2 -5.1 0.7 -4.4 -6.0 0.8 -5.2 -7.8
P(OC3H7)3 -4.6 -0.5 -5.1 -4.5 1.3 -3.2 -5.6 1.4 -4.2 -6.1
Mean unsigned error 0.6 1.1 1.0
compounds without C or P
ammonia -0.1 -6.1 -6.1 -0.3 -4.0 -4.3 0.0 -4.3 -4.3 -4.3
water -1.2 -7.4 -8.6 -1.2 -5.1 -6.3 -1.9 -4.4 -6.3 -6.3
hydrogen sulfide -0.2 -0.5 -0.7 -0.2 -0.7 -0.9 0.0 -0.8 -0.8 -0.7
Mean unsigned error 1.0 0.07 0.03
Mean unsigned error all compounds 0.6 0.7 0.9
RMS error all compounds 0.8 0.9 1.3
Table 6. Calculated and experimental free energies of solvation (kcal/mol) for
ions used in the parameterization of SM2 and SM3.
SM1 SM2 SM3 Expt a
Compound A B C A B C A B C C
H- -89.0 0.0 -89.0 -89.0 0.0 -89.0 -89.0 0.0 -89.0 -89
F- -106.9 1.9 -105.0 -109.2 2.2 -107.0 -109.0 2.0 -107.0 -107
Cl- -74.7 -0.3 -75.0 -76.7 -0.3 -77.0 -76.5 -0.5 -77.0 -77
Br- -68.8 -1.2 -70.0 -70.8 -1.2 -72.0 -71.3 -0.7 -72.0 -72
I- -59.8 -1.2 -61.0 -60.8 -2.2 -63.0 -62.6 -0.4 -63.0 -63
OH- -105.0 -4.2 -109.2 -99.9 -8.2 -108.1 -103.9 -7.5 -111.4 -106
CN- -75.9 -3.1 -79.0 -80.8 -2.6 -83.5 -76.2 -3.4 -79.6 -77
O2- -84.4 -6.8 -91.2 -84.3 -3.8 -88.1 -79.5 -5.4 -84.9 -87
HS- -73.7 -1.9 -75.6 -74.4 -1.9 -76.3 -74.7 -1.9 -76.7 -76
PH2- -68.0 0.9 -67.1 -67.6 0.6 -67.0 -68.4 1.6 -66.8 -67
HC2- -78.4 1.8 -76.6 -78.5 0.7 -77.8 -78.0 1.2 -76.8 -73
HO2- -95.8 -5.5 -101.4 -90.0 -7.0 -97.0 -82.1 -7.4 -89.5 -101
N3- -63.6 -11.3 -74.9 -69.5 -5.7 -75.2 -64.7 -7.9 -72.6 -74
NO2- -74.8 -8.6 -83.4 -73.0 -4.7 -77.7 -70.4 -6.5 -76.9 -72
CH3O- -86.1 -2.8 -88.9 -81.3 -2.2 -83.5 -79.0 -2.6 -81.6 -95
NO3- -55.4 -9.1 -64.5 -54.5 -5.0 -59.0 -40.7 -7.1 -47.7 -65
CH2CN- -64.9 -3.5 -68.4 -67.3 -2.4 -69.7 -67.8 -3.5 -71.3 -75
CH3CO2- -74.5 -5.0 -79.5 -72.9 -3.0 -75.9 -71.3 -4.3 -75.5 -77
H3O+ -100.6 -1.6 -102.1 -100.0 -3.8 -103.8 -98.9 -3.5 -102.4 -104
NH4+ -77.8 -0.4 -78.2 -77.3 -1.7 -79.0 -71.2 -10.5 -81.7 -79
MeOH2+ -79.8 -0.8 -80.5 -79.0 -5.2 -84.2 -81.5 -3.5 -84.6 -83
MeSH2+ -73.6 -0.8 -74.4 -73.7 0.1 -73.6 -76.7 0.1 -76.6 -74
MeNH3+ -69.7 0.0 -69.6 -68.6 -3.3 -71.9 -64.7 -2.4 -67.1 -70
Me2OH+ -61.3 -0.2 -61.5 -60.9 -1.8 -62.8 -67.5 -1.6 -69.1 -70
Me2NH2+ -61.0 0.3 -60.7 -61.3 -2.0 -63.3 -60.0 -3.1 -63.1 -63
Me3NH+ -53.2 0.3 -52.9 -53.9 0.2 -53.7 -54.3 -0.2 -54.5 -59
Me3PH+ -49.6 0.2 -49.4 -49.4 1.5 -47.9 -58.8 1.8 -57.0 -53
CH3C(OH)NH2+ -60.6 -2.3 -62.9 -60.4 -7.8 -68.2 -66.6 -9.0 -75.6 -66
Mean unsigned error 2.9 2.6 3.5
RMS error 4.0 3.9 5.6
a From Pearson, R. G., J. Amer. Chem. Soc., 108 (1986) 6109.
Errors may be substantial (+/- 5 kcal/mol).
Table 7. Calculated and experimental free energies of solvation for additional
ions.
SM1 SM2 SM3 Expt a
Compound A B C A B C A B C C
CH3- -68.1 0.7 -67.4 -68.4 0.9 -67.5 -83.5 1.0 -82.5 -82
PH4+ -63.5 0.4 -63.1 -61.4 0.6 -60.8 -61.0 1.6 -59.4 -73
MePH3+ -59.8 0.3 -59.5 -57.8 0.8 -57.0 -59.6 1.7 -657.9 -66
Me2PH2+ -54.3 0.2 -54.1 -51.1 1.2 -49.9 -61.0 1.8 -59.2 -57
H2PO4- -120.8 -8.1 -128.9 -95.5 -10.0 -105.5 -75.4 -10.7 -86.1
HPO42- -223.6 -9.5 -333.1 -291.5 -8.0 -299.5 -256.5 -9.4 -265.9
PO43- -665.0 -10.6 -675.5 -623.5 -5.7 -629.1 -562.4 -8.1 -570.5
SH3+ -76.3 -1.1 -77.3 -76.4 -0.3 -76.7 -82.1 -0.4 -82.5 -87
a When given, from Pearson, but considered uncertain or unreliable (see text). In other cases, unavailable.
Table 8. Calculated and experimental free energies of solvation for additional neutral solutes (kcal/mol)
SM1 SM2 SM3 Expt.
Compound A B C A B C A B C C
H2NCH2COOH -4.1 -5.0 -9.1 -4.0 -9.8 -13.8 -3.0 -11.4 -14.4
+H3NCH2COO- -41.3 -4.8 -46.1 -39.5 -6.2 -45.7 -34.5 -6.5 -40.1
E-N-methylformamide -8.7 -2.7 -11.4 -8.7 -3.5 -12.2 -7.2 -4.7 -11.8 -10.0a
glycoaldehyde -3.5 -4.0 -7.5 -3.4 -5.8 -9.1 -4.1 -5.9 -10.0
deoxycytidine -12.5 -7.3 -19.8 -12.5 -14.2 -26.7 -12.1 -16.3 -28.4
(CH3)3P -0.5 0.6 0.1 -0.5 1.5 1.0 -0.8 1.9 1.1 -0.9b
H3PO4 -57.2 -6.9 -64.1 -39.7 -12.4 -52.1 -22.8 -12.0 -34.8
1-pentanol -0.8 -1.4 -2.2 -0.8 -3.3 -4.1 -1.0 -2.9 -3.9 -4.5c
2-pentanol -0.6 -1.1 -1.7 -0.6 -2.4 -2.9 -0.6 -2.0 -2.7 -4.4c
3-pentanol -0.5 -0.8 -1.3 -0.5 -2.0 -2.4 -0.6 -1.7 -2.3 -4.4c
cyclopentanol -0.8 -1.5 -2.3 -0.7 -3.1 -3.8 -0.7 -2.6 -3.3 -5.5c
pentanal -2.5 -2.0 -4.4 -2.5 -0.6 -3.1 -2.9 -1.0 -3.9 -3.0c
cyclopentanone -3.0 -2.3 -5.3 -3.0 -0.8 -3.8 -3.1 -1.3 -4.4
a
Yu. H.-A., Pettit, B. M. and Karplus, M., J. Amer. Chem. Soc., 113 (1991) 2425.
b Estimate from Pearson.
c From :
Hine J. and Mookerjee, P. K., J. Org. Chem., 40 (1975) 287.
Cabani, S., Gianni, P., Mollica, V. and Lepori, L., J. Solution Chem., 10
(1981) 563.
Ben-Naim, A. and Marcus, Y., J. Chem. Phys., 81 (1984) 2016.
Table 9. Free energy of solvation changes (kcal/mol) in acid-base equilibria.
Reaction Expt SM1 SM2 SM3
NH4+ + aniline -> NH3 + aniline*H+ 12.9 16.5 16.5 23.1
NH4+ + MeNH2 -> NH3 + MeNH3+ 9.6 8.7 8.9 16.6
NH4+ + pyridine -> NH3 + pyridine*H+ 25.1 23.3 21.2 20.2
NH4+ + Me2NH -> NH3 + Me2NH2+ 17.6 18.0 15.7 17.3
NH4+ + Me3N -> NH3 + Me3NH+ 23.7 26.1 23.6 23.1
NH4+ + PhCO2- -> NH3 + PhCO2H 137.3 143.8 138.7 141.8
NH4+ + AcO- -> NH3 + AcOH 146.9 149.0 142.9 144.4
NH4+ + PhO- -> NH3 + PhOH 141.1 140.6 134.1 138.3
NH4+ + Cp- -> NH3 + CpHb 137.6 134.8 133.1 139.8
aniline*H+ + MeNH2 -> aniline+ MeNH3+ -3.3 -7.7 -7.6 -6.5
aniline*H+ + pyridine -> aniline+ pyridine*H+ 12.2 6.9 4.7 -2.9
aniline*H+ + Me2NH -> aniline+ Me2NH2+ 4.7 1.6 -0.8 -5.8
aniline*H+ + Me3N -> aniline+ Me3NH+ 10.8 9.8 7.1 0.0
aniline*H+ + PhCO2- -> aniline+ PhCO2H 124.4 127.4 122.2 118.7
aniline*H+ + AcO- -> aniline+ AcOH 134.0 132.6 126.4 121.3
aniline*H+ + PhO- -> aniline+ PhOH 128.2 124.0 117.6 115.2
aniline*H+ + Cp- -> aniline+ CpH 124.7 118.5 116.6 116.7
MeNH3+ + pyridine -> MeNH2+ pyridine*H+ 15.5 14.6 12.3 3.6
MeNH3+ + Me2NH -> MeNH2+ Me2NH2+ 8.0 9.4 6.8 0.7
MeNH3+ + Me3N -> MeNH2+ Me3NH+ 14.1 17.4 14.7 6.5
MeNH3+ + PhCO2- -> MeNH2+ PhCO2H 127.7 135.2 129.8 125.2
MeNH3+ + AcO- -> MeNH2+ AcOH 137.3 140.4 134.0 127.8
MeNH3+ + PhO- -> MeNH2+ PhOH 131.6 131.7 125.2 121.7
MeNH3+ + Cp- -> MeNH2+ CpH 128.0 126.2 124.2 123.2
pyridine*H+ + Me2NH -> pyridine+ Me2NH2+ -7.6 -5.3 -5.5 -2.9
pyridine*H+ + Me3N -> pyridine+ Me3NH+ -1.4 2.9 2.4 2.9
pyridine*H+ + PhCO2- -> pyridine+ PhCO2H 112.2 120.6 117.5 121.6
pyridine*H+ + AcO- -> pyridine+ AcOH 121.8 125.8 121.7 124.2
pyridine*H+ + PhO- -> pyridine+ PhOH 116.0 117.1 112.9 118.1
pyridine*H+ + Cp- -> pyridine+ CpH 112.5 111.6 111.9 119.6
Me2NH2+ + Me3N -> Me2NH+ Me3NH+ 6.2 8.2 7.9 5.8
Me2NH2+ + PhCO2- -> Me2NH+ PhCO2H 119.7 125.8 123.0 124.5
Me2NH2+ + AcO- -> Me2NH+ AcOH 129.3 131.1 127.2 127.1
Me2NH2+ + PhO- -> Me2NH+ PhOH 123.5 122.4 118.4 121.0
Me2NH2+ + Cp- -> Me2NH+ CpH 121.0 116.9 117.4 122.5
Me3NH+ + PhCO2- -> Me3N+ PhCO2H 113.7 117.6 115.1 118.7
Me3NH+ + AcO- -> Me3N+ AcOH 123.2 122.9 119.3 121.3
Me3NH+ + PhO- -> Me3N+ PhOH 117.4 114.3 110.5 115.2
Me3NH+ + Cp- -> Me3N+ CpH 114.9 108.7 109.5 116.7
PhCO2H + AcO- -> PhCO2-+ AcOH 9.4 5.3 4.2 2.6
PhCO2H + PhO- -> PhCO2-+ PhOH 3.7 -3.5 -4.6 -3.5
PhCO2H + Cp- -> PhCO2-+ CpH 1.3 -8.9 -5.6 -2.0
AcOH+ PhO- -> AcO-+ PhOH -5.7 -8.6 -8.8 -6.1
AcOH+ Cp- -> AcO-+ CpH -8.1 -14.2 -9.8 -4.6
PhOH+ Cp- -> PhO-+ CpH -2.4 -5.5 -1.0 1.5
Mean unsigned error 3.6 3.8 5.4
RMS error 4.4 4.5 6.6