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Abraham Article
Abraham Article
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Abstract
Ostwald solubility coecients of 74 compounds in dry octan-1-ol at 298 K have been determined, and have been
combined with literature values and additional values we have calculated from solubilities in dry octan-1-ol and vapour
pressures to yield a total of 161 log LOctOH values at 298 K. These LOctOH values are identical to gas-to-dry octan-1-ol
partition coecients, often denoted as KOA . Application of the solvation equation of Abraham to 124 values as a
training set yielded a correlation equation with n 124, S:D: 0:125, r2 0:9970 and F 7731. This equation was
then used to predict 32 values of log LOctOH as a test set, giving a standard deviation, S.D. of 0.131, an average absolute
deviation of 0.085 and an average deviation of )0.009 log units. The solvation equation for the combined 156 log LOctOH
values was
log LOctOH 0:1200:203R2 0:560pH
X X2 H
3:560 aH
2 0:702 b2
0:939 log L16 ;
n 156; r2 0:9972; S:D: 0:125;
F 10573;
where, n is the number of data points (solutes), r the correlation coecient, S.D. the standard deviation and F is the F-
statistic. The independent
P H is an excess molar refraction, pH
variables are solute descriptors as follows: R2P 2 the dipolarity/
polarisability, a2 the overall or summation hydrogen-bond acidity, bH
2 the overall or summation hydrogen-bond
basicity and L16 is the Ostwald solubility coecient on hexadecane at 298 K. The equation is consistent with similar
equations for the solubility of gases and vapours into methanol, ethanol and propan-1-ol. It is suggested that the
equation can be used to predict further values of log LOctOH , for which the solute descriptors are known, to within 0.13
log units. Ó 2001 Elsevier Science Ltd. All rights reserved.
1. Introduction
*
Corresponding author. Tel.: +44-020-7679-4684; fax: +44-
020-7679-7463. The water±octanol partition system is widely used
E-mail address: m.h.abraham@ucl.ac.uk (M.H. Abraham). as a model for a wide variety of processes in which
0045-6535/01/$ - see front matter Ó 2001 Elsevier Science Ltd. All rights reserved.
PII: S 0 0 4 5 - 6 5 3 5 ( 0 0 ) 0 0 2 8 8 - 5
856 M.H. Abraham et al. / Chemosphere 44 (2001) 855±863
Table 1
Calculation of log L in dry octan-1-ol at 298 K
Solute log Soct a log CG log Loct
b
Naphthalene )0.15 )5.34 5.19
Anthracene )1.91 )9.46b 7.55
Phenanthrene )0.45 )7.97b 7.52 7.57c
Acenaphthene )0.59 )6.9b 6.31
Fluorene )0.62 )7.45d; e 6.83 6.79c
Fluoranthene )0.76 )9.37e 8.61
Pyrene )0.90 )9.65b 8.75 8.80c
Biphenyl )0.13 )6.28e 6.15
1,4-Dichlorobenzene 0.20 )4.26e; f 4.46
1,3,5-Trichlorobenzene )0.16g )5.01e 4.85
1,2,3,5-Tetrachlorobenzene 0.15 )5.40d; e 5.55
1,2,4,5-Tetrachlorobenzene )0.92 )6.54h 5.62 (5.63h )
1,2,3,4-Tetrachlorobenzene (5.64h )
Pentachlorobenzene )0.56 )7.05h 6.49 (6.27h )
Hexachlorobenzene )1.86 )9.03h 7.17 (6.90h )
Hexamethylbenzene )0.89 )7.20e 6.31
1,4-Dibromobenzene )0.30 )5.51e 5.21
Hexachloroethane )0.28 )4.75d; e 4.47
4-Ethoxyacetanilide )0.84 )10.43e 9.59
Diphenylamine 0.03 )7.61e 7.64
trans-Stilbene )1.10i )8.58i 7.48
4-Hydroxybenzoic acid )0.17j; k )8.25b 8.08
2-Hydroxybenzoic acid 0.17l )7.27b 7.44
Methyl 4-hydroxybenzoate )0.10j; k )8.67b 8.57
a
All data from Tse and Sandler (1994), unless shown otherwise.
b
Abraham et al. (1999).
c
Directly determined values from Harner and Bidleman (1998).
d
Mackay and Shiu (1981).
e
Stephenson and Malinowski (1987).
f
Rordorf (1985).
g
Yalkowsky et al. (1994).
h
Harner and Mackay (1995). The values in parentheses are directly determined ones.
i
Abraham et al. (1998).
j
Martin et al. (1984).
k
Alexander et al. (1977).
l
Acree (unpublished).
on hexadecane at 298 K (Abraham et al., 1987), de®ned head-space is sampled to a Hewlett-Packard 5890 gas
similarly to Eq. (1). Descriptors for several hundred chromatograph by a vacuum transfer sampling system
solutes have been published (Abraham, 1993; Abraham connected to the sample cell through a series of heated
et al., 1994), and the entire data base of descriptors is fused silica transfer lines. The sampling system consists
now commercially available (Abraham, 2000). of a series of heated valves (Valco Instruments, Hous-
Eq. (3) has already been applied to the solubility of ton, TX) and a mechanical vacuum pump (Welch Duo-
gases and vapours in water (Abraham et al., 1994), Seal). Each of the homologous series of solutes were run
methanol (Abraham et al., 1998a), ethanol (Abraham as a group, and were separated using a methyl silicone
et al., 1998b), and propan-1-ol (Abraham et al., 1999), capillary column, with ¯ame ionisation detection; the
as well as to numerous sets of gas-chromatographic signal was recorded and integrated by a Hewlett-Pack-
data, so it is a well-tried and tested equation. ard 3396 integrator.
The sample cell (60 ml) was thermostatted by a water
jacket at 25:00 0:02°C and the cell temperature was
3. Experimental monitored with a calibrated calorimetric thermometer
(Brooklyn Thermometer, Brooklyn, NY). Anhydrous
The head-space gas-chromatographic apparatus, octan-1-ol (40 ml; < 0:005% water; Aldrich Chemical)
measurement techniques, and calculations are as previ- was pipetted into the cell, and stirred using a glass-
ously described in detail (Dallas, 1995). In brief, the encapsulated magnetic stirrer. Typically, ®ve increments
858 M.H. Abraham et al. / Chemosphere 44 (2001) 855±863
Table 2
Values of log L in dry octan-1-ol at 298 K
Solute log L References
a
Helium )1.72 Wilcock et al. (1978), Harner and Mackay (1995)
Neon )1.57 Bo et al. (1993)b
Argon )0.71 Bo et al. (1993)b
Krypton )0.24 Bo et al. (1993)b
b
Xenon 0.38
Hydrogena )1.29 b
Table 2 (Continued)
Solute log L References
Tetrahydrofuran 2.86 This work
Tetrahydropyran 3.22 This work
Dioxane 3.17 This work
Propanonea 2.31 This work
Butanone 2.77 This work
Pentan-2-one 3.19 This work
Pentan-3-one 3.20 This work
3-Methylbutan-2-one 3.04 This work
Hexan-2-onea 3.68 This work
Heptan-2-one 4.15 This work
Cyclopentanone 3.67 This work
Methyl formate 1.75 This work
Ethyl formate 2.19 This work
Propyl formatea 2.66 This work
Methyl acetate 2.31 This work
Ethyl acetate 2.70 This work
Propyl acetate 3.17 This work
Butyl acetate 3.65 This work
Pentyl acetatea 4.12 This work
Hexyl acetate 4.58 This work
Isopropyl acetate 2.93 This work
Isobutyl acetate 3.45 This work
Isopentyl acetate 3.94 This work
Ethyl propanoatea 3.15 This work
Ethyl butanoate 3.56 This work
Acetonitrile 2.31 This work
Proprionitrile 2.69 This work
Butanonitrile 3.12 This work
2-Cyanopropanea 2.87 This work
Pentanonitrile 3.60 This work
Hexanonitrile 4.08 This work
e
Butylamine 3.61
b
Methylamine 1.90
Dimethylaminea 2.00 b
e
Dipropylamine 3.59
Nitromethane 2.52 This work
Nitroethane 2.88 This work
Nitropropane 3.25 This work
Dimethylformamidea 4.38 This work
Methanol 2.84 This work
Ethanol 3.20 This work
Propan-1-ol 3.68 This work
Propan-2-ol 3.38 This work
Butan-1-ola 4.19 This work
2-Methylpropan-1-ol 3.93 This work
Butan-2-ol 3.80 Cabani et al. (1991), Gruber et al. (1997)
2-Methylpropan-2-ol 3.50 This work
Pentan-1-ol 4.69 This work
3-Methylbutan-1-ola 4.52 This work
Hexan-1-ol 5.18 This work
Octan-1-ol 6.03 Cabani et al. (1991)
Hexadecan-1-ol 9.90 Table 1
Octadecan-1-ol 10.93 Table 1
Eicosan-1-ola 12.06 Table 1
2-Chloroethanol 4.30 Table 1
Cyclohexanol 5.18 This work
Acetic acid 4.31 This work
Dimethylsulfoxide 4.96 This work
860 M.H. Abraham et al. / Chemosphere 44 (2001) 855±863
Table 2 (Continued)
Solute log L References
Sulphur hexa¯uoridea )0.30 Wilcock et al. (1978), Bo et al. (1993)
Carbon disulphide 2.28 Thomas et al. (1982)
f
Tetramethyltin 2.62
Benzene 2.80 This work
Toluene 3.31 This work
Ethylbenzenea 3.72 Tewari et al. (1982), Gruber et al. (1997)
o-Xylene 3.90 Tewari et al. (1982), Gruber et al. (1997)
m-Xylene 3.79 Tewari et al. (1982), Gruber et al. (1997)
p-Xylene 3.79 Gruber et al. (1997)
Propylbenzene 4.09 Tewari et al. (1982)
Isopropylbenzenea 3.98 Tewari et al. (1982)
Hexamethylbenzene 6.31 Table 1
trans-Stilbene 7.48 Table 1
Biphenyl 6.15 Table 1
Naphthalene 5.19 Table 1
Acenaphthenea 6.31 Table 1
Fluorene 6.83 Table 1
Anthracene 7.55 Table 1
Phenanthrene 7.52 Table 1
Fluoranthene 8.61 Table 1
Pyrenea 8.75 Table 1
1,2-Dichlorobenzene 4.36 Table 1
1,4-Dichlorobenzene 4.46 Table 1
1,2,3-Trichlorobenzene 5.19 Table 1
1,3,5-Trichlorobenzene 4.85 Table 1
1,2,3,4-Tetrachlorobenzenea 5.64 Table 1
1,2,3,5-Tetrachlorobenzene 5.55 Table 1
1,2,4,5-Tetrachlorobenzene 5.62 Table 1
Pentachlorobenzene 6.49 Table 1
Hexachlorobenzene 7.17 Table 1
1,4-Dibromobenzenea 5.21 Table 1
Anisole 4.01 This work
a
Benzonitrile 4.46
Diphenylamine 7.64 Table 1
4-Ethoxyacetanilide 9.59 Table 1
4-Hydroxybenzoic acid 8.08 Table 1
2-Hydroxybenzoic acida 7.44 Table 1
Methyl 4-hydroxybenzoate 8.57 Table 1
Piperidine 4.04 Cabani et al. (1991)
N-Methylpyrrolidine 3.64 Cabani et al. (1991)
Pyrrolidinea 4.07 Cabani et al. (1991)
Dimethylacetamide 5.33 This work
Propanal 3.02 This work
Butanal 3.39 This work
Hexanal 4.41 This work
Octanal 5.36 This work
a
Test set.
b
Solubility data project.
c
Boyer and Bircher (1960).
d
Gerrard (1972).
e
Personal communication from Prof. Cabani.
f
Abraham (1972).
of a solute mixture (100 ll), prepared gravimetrically, space (400 ll) is vacuum transferred to a sample loop
were added to the octanol using a computer controlled (100 ll) and injected into the chromatograph.
autotitrator (Model ABU-11, Radiometer, Copenhagen, External standards of the vapour phase were pre-
Denmark). After equilibration, a sample of the head- pared gravimetrically by addition of a known amount of
M.H. Abraham et al. / Chemosphere 44 (2001) 855±863 861
Table 3
Observed log LOctOH and calculated values on Eq. (4) for the test set
Solute Obs. Calc. Obs. ) calc.
Helium )1.72 )1.730 0.010
Hydrogen )1.29 )1.226 )0.064
Carbon dioxide 0.16 0.354 )0.194
Pentane 1.95 1.907 0.043
Methylcyclohexane 3.05 2.976 0.074
Non-1-ene 3.83 3.766 0.064
Dichloromethane 2.27 2.420 )0.150
1,1,1-Trichloroethane 2.70 2.669 0.031
1-Chlorobutane 2.72 2.688 0.032
Bromoethane 2.11 2.114 )0.004
Diethylether 2.19 2.220 )0.030
Dipentylether 4.80 4.893 )0.093
Propanone 2.31 2.324 )0.014
Hexan-2-one 3.68 3.651 0.029
Propyl formate 2.66 2.760 )0.100
Pentyl acetate 4.12 4.118 0.002
Ethyl propanoate 3.15 3.137 0.013
2-Cyanopropane 2.87 2.898 )0.028
Dimethylamine 2.00 2.269 )0.269
Dimethylformamide 4.38 4.046 0.334
Butan-1-ol 4.19 4.171 0.019
3-Methylbutan-1-ol 4.52 4.541 )0.021
Eicosan-1-ol 12.06 11.723 0.337
Sulphur hexa¯uoride )0.30 )0.439 0.139
Ethylbenzene 3.72 3.698 0.022
Isopropylbenzene 3.98 3.981 )0.001
Acenaphthene 6.31 6.385 )0.075
Pyrene 8.75 8.790 )0.040
1,2,3,4-Tetrachlorobenzene 5.64 5.954 )0.314
1,4-Dibromobenzene 5.21 5.164 0.046
2-Hydroxybenzoic acid 7.44 7.408 0.032
Pyrrolidine 4.07 4.175 )0.105
the solute mixture to a 12 l glass bulb, and allowed to pounds and a randomly chosen test set of 32
vapourise completely. A sample of the standard vapour compounds, as shown in Table 2. Application of the
is transferred to the chromatograph exactly as for the solvation Eq. (3) to the training set yielded the correla-
test samples. Each measurement of LOctOH was carried tion equation
out at ®ve dierent solute concentrations. No depen-
dence on solute concentration was noted, and the LOctOH log LOctOH 0:108 0:177 R2 0:567 pH
X X H2
values were taken to be those at in®nite dilution. The 3:565 aH2 0:703 b2
octan-1-ol was stored over molecular sieve 4A, and the
0:932 log L16 ;
purity of the octan-1-ol and of the solutes was checked
by gas chromatography. n 124; r2 0:9970;
S:D: 0:125; F 7731;
4
Table 5
Coecients in Eq. (3) for gas±solvent partitions
Solvent c r s a b l
Water )1.271 0.822 2.743 3.904 4.814 )0.213
Methanol )0.004 )0.215 1.173 3.701 1.432 0.769
Ethanol 0.012 )0.206 0.789 3.635 1.311 0.853
Propan-1-ol )0.028 )0.185 0.648 4.022 1.043 0.869
Octan-1-ol )0.120 )0.203 0.560 3.576 0.702 0.939
where, n is the number of data points (solutes), r the are in Table 5. There is a gradual progression in the
correlation coecient, S.D. the standard deviation and coecients from solvent water to solvent octan-1-ol,
F is the F-statistic. The goodness-of-®t of Eq. (4) is ex- with the minor exception of the a-coecient for propan-
cellent. Of the ®ve outliers to Eq. (4), four were the 1-ol. The coecients in Eq. (5) are quite in line with
aliphatic aldehydes; it is known that these compounds those for the other alcohols we have studied, so that Eq.
form aldols with aliphatic alcohols, and so their exclu- (5) is chemically reasonable, as well as being statistically
sion is warranted on chemical grounds. The other outlier very good. As for the other dry alcohols in Table 5, bulk
was dimethylacetamide, but its log LOctOH value is so octan-1-ol is shown to be weakly dipolar/polarisable, a
large that there is considerable experimental uncertainty strong hydrogen-bond base, and only a moderate-to-
here. weak hydrogen-bond acid. The l-coecient indicates
A standard method of assessing the predictive capa- that as the alcohol chain length increases, the bulk al-
bility of an equation is to apply it to a test set of com- cohol functions more and more as a lipophilic solvent;
pounds not used to set up the equation. For the 32 data note that for solvent hexadecane l 1 by de®nition.
test set that we set aside, values of log LOctOH were
predicted through Eq. (4), and the predicted and ob-
served values were compared, see Table 3. The standard Acknowledgements
deviation between predicted and observed log LOctOH
values is only 0.131, the average absolute deviation is We are grateful to Roche Products Ltd., for a re-
0.085, and the average deviation is )0.009 log units. It is search studentship (to J.L.), and we thank the late Prof.
therefore clear that log LOctOH values can be predicted Sergio Cabani for a number of log LOctOH values.
through Eq. (4) to around 0.13 log units, for any solute
for which descriptors are available. In Table 4, we give
details of the number of solutes for which we have the References
relevant descriptors. Even with the proviso that the
compound descriptors are within the descriptor space of Abraham, M.H., 1971. Substitution at saturated carbon. Part
the solutes used to set up the correlation equation, it is IX. Free energies of transfer from methanol to aqueous
evident that values of log LOctOH can be predicted for a methanol of tetra-alkyltins and the transition states in the
huge number of compounds. bimolecular substitution of tetra-alkyltins by mercuric
chloride. J. Chem. Soc. A, 1061±1068.
We can combine the training set and the test set to
Abraham, M.H., 1972. J. Chem. Soc., Perkin Trans. II, 1343±
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5
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