Electronic Supplementary Material (ESI) for Chemical Science This journal is © The Royal Society of Chemistry 2013 1 Supplementary Information A Surface Site Interaction Model for the Properties of Liquids at Equilibrium Christopher A. Hunter* Department of Chemistry, University of Sheffield, Sheffield S3 7HF (UK). Table S1. Experimental free energies of transfer measured at 298 K in kJ mol-1 (mole fraction standard state). transfer of liquid liquid liquid liquid liquid liquid n-octane water ethanol to liquid liquid liquid liquid n-hexadecane 1-octanol n-octane water ethanol from n-hexadecane water 1-octanol diethyl ether water water liquid liquid liquid liquid n-pentane -0.4 28.7 3.9 29.0 24.7 19.0 10.6 2-methylbutane 28.1 28.4 19.5 n-hexane -0.3 31.9 4.3 32.6 27.7 0.0 18.7 7.8 cyclohexane -0.6 26.7 1.6 29.0 25.0 -0.3 20.5 9.6 n-heptane -0.2 35.4 3.4 36.2 32.0 18.8 10.0 n-octane -0.2 39.7 4.8 -0.1 40.0 35.0 0.2 18.4 9.7 2,2,4-trimethylpentane 36.7 36.8 19.7 n-decane 49.8 46.9 0.2 18.5 8.1 n-dodecane 53.7 18.4 9.3 n-hexadecane -0.2 18.1 8.8 water 18.0 0.0 6.0 -18.0 -3.2 39.8 3.2 methanol 10.2 1.0 0.1 2.9 -8.9 1.0 ethanol 8.8 0.6 -3.0 1.4 -5.5 3.6 7.1 5.2 0.2 1-propanol 7.9 6.4 -0.4 1.9 -1.8 6.8 5.9 -0.3 2-propanol 7.6 7.5 1.8 1.9 -2.9 5.7 5.3 0.3 1-butanol 8.0 9.8 -0.6 1.6 2.0 10.4 5.1 1.6 -0.9 2-methyl-1-propanol 4.4 9.1 1.9 2-butanol 6.8 8.4 0.9 0.7 2-methyl-2-propanol 6.6 0.6 -0.6 1-pentanol 7.5 13.4 -0.9 2.3 5.5 14.3 3.1 3-methyl-1-butanol 9.0 12.9 5.6 2.7 2-methyl-2-butanol 5.9 9.2 3.4 1.3 1-hexanol 7.3 16.6 -0.4 1.9 9.1 17.0 2.9 cyclohexanol 7.4 12.3 -0.1 5.5 12.4 2.1 1-octanol 7.7 24.9 2.4 6.3 16.2 22.5 4.9 3.2 0.5 1-decanol 6.9 30.7 -0.8 23.8 31.5 3.5 1-dodecanol 36.4 1.7 34.7 5.6 Electronic Supplementary Material (ESI) for Chemical Science This journal is © The Royal Society of Chemistry 2013 2 2-methoxyethanol 2.9 -7.2 8.6 0.8 2-ethoxyethanol -5.1 ethylene glycol 10.1 1,2-propanediol 1,3-propanediol 1,2-butanediol 2R,3S-butanediol 1,4-butanediol 1,5-pentanediol diethylene glycol triethylene glycol diethyl ether 0.1 10.4 -0.1 0.2 11.8 10.5 -0.1 7.1 1.4 di-n-propyl ether 0.0 17.5 0.5 18.9 17.0 9.1 diisopropyl ether 0.4 15.2 1.2 18.9 14.1 0.1 8.6 2.7 dibutyl ether -0.3 25.0 1.2 25.8 23.8 0.3 10.7 3.9 1,2-dimethyoxyethane diethylene glycol dimethyl ether tetrahydrofuran 0.0 7.2 -0.9 7.4 8.1 1.5 1.4 2-methyltetrahydrofuran 8.5 9.2 3.6 tetrahydropyran -3.5 10.0 -0.8 11.3 10.8 5.0 Table S2. Calculated free energies of transfer measured at 298 K in kJ mol-1 (mole fraction standard state). transfer of liquid liquid liquid liquid liquid liquid n-octane water ethanol to liquid liquid liquid liquid n-hexadecane 1-octanol n-octane water ethanol from n-hexadecane water 1-octanol diethyl ether water water liquid liquid liquid liquid n-pentane -0.3 26.7 0.3 -0.8 27.0 26.4 0.4 19.4 9.1 2-methylbutane -0.4 26.7 0.3 -0.9 27.0 26.4 0.5 19.4 9.2 n-hexane -0.3 30.5 0.4 -1.0 30.8 30.1 0.3 19.4 9.1 cyclohexane 0.0 27.0 0.6 -0.6 27.0 26.4 0.0 19.3 8.9 n-heptane -0.4 34.3 0.4 -1.2 34.6 33.8 0.3 19.3 9.0 n-octane -0.1 40.5 0.9 -0.9 40.5 39.6 0.0 19.3 8.9 2,2,4-trimethylpentane -0.6 35.7 0.2 -1.7 36.3 35.5 0.5 19.3 9.0 n-decane -0.2 48.0 1.0 -1.2 48.1 47.0 0.0 19.3 8.9 n-dodecane -0.2 55.6 1.1 -1.5 55.7 54.4 0.0 19.3 8.9 n-hexadecane 0.0 73.7 1.8 -1.0 73.7 71.8 -0.1 19.2 9.0 water 19.2 0.0 6.4 3.0 -19.2 -6.4 40.5 0.0 3.3 methanol 9.6 0.2 2.0 2.3 -9.4 -1.8 2.1 0.8 -0.5 Electronic Supplementary Material (ESI) for Chemical Science This journal is © The Royal Society of Chemistry 2013 3 ethanol 9.0 3.3 1.5 1.6 -5.6 1.9 2.3 2.2 0.0 1-propanol 8.5 6.7 1.1 1.0 -1.9 5.6 2.1 3.2 0.3 2-propanol 8.4 6.6 1.0 0.9 -1.9 5.6 2.2 3.3 0.4 1-butanol 8.1 10.0 0.7 0.4 1.9 9.3 1.9 4.1 0.6 2-methyl-1-propanol 8.0 10.0 0.7 0.3 1.9 9.3 1.9 4.1 0.6 2-butanol 8.1 10.0 0.7 0.4 1.9 9.3 1.9 4.1 0.6 2-methyl-2-propanol 7.9 9.9 0.6 0.3 1.9 9.3 2.1 4.1 0.7 1-pentanol 7.7 13.4 0.4 -0.1 5.7 13.0 1.7 4.8 0.9 3-methyl-1-butanol 7.7 13.4 0.4 -0.2 5.7 13.0 1.7 4.8 0.9 2-methyl-2-butanol 7.6 11.2 0.2 -0.4 3.6 11.0 2.5 4.6 1.0 1-hexanol 7.4 16.9 0.2 -0.6 9.5 16.7 1.5 5.4 1.1 cyclohexanol 7.9 13.7 0.6 0.1 5.7 13.0 1.4 4.7 0.7 1-octanol 7.0 26.2 0.0 -1.1 19.2 26.2 0.9 6.4 1.5 1-decanol 6.5 33.4 -0.3 -1.9 26.8 33.6 0.8 7.2 1.8 1-dodecanol 6.1 40.5 -0.6 -2.6 34.4 41.1 0.7 7.8 2.1 2-methoxyethanol 10.7 -5.9 0.3 3.3 -16.6 -6.2 -0.1 -0.5 -0.6 2-ethoxyethanol 10.3 -2.4 0.1 2.8 -12.8 -2.5 0.5 0.4 -0.2 ethylene glycol 21.3 -5.7 5.8 6.6 -26.9 -11.5 4.7 -0.9 -0.5 1,2-propanediol 20.3 -2.9 4.9 5.4 -23.2 -7.8 4.5 0.2 -0.3 1,3-propanediol 20.4 -2.8 5.0 5.5 -23.2 -7.8 4.4 0.2 -0.3 1,2-butanediol 19.5 0.1 4.2 4.5 -19.4 -4.1 4.0 1.0 -0.2 2R,3S-butanediol 19.4 -1.9 4.0 4.5 -21.3 -5.9 4.7 0.9 0.1 1,4-butanediol 19.5 0.2 4.2 4.6 -19.4 -4.1 4.0 1.0 -0.2 1,5-pentanediol 18.8 3.3 3.6 3.7 -15.6 -0.3 3.5 1.7 -0.1 diethylene glycol 21.3 -12.6 3.2 6.7 -33.8 -15.7 0.9 -1.2 -0.9 triethylene glycol 21.6 -17.2 0.8 7.0 -38.8 -18.1 -0.7 -1.2 -1.0 diethyl ether 0.2 8.8 -2.1 0.0 8.5 10.8 -0.9 3.0 1.6 di-n-propyl ether 0.5 18.7 -1.6 0.1 18.3 20.3 -0.9 4.5 2.2 diisopropyl ether 0.1 16.2 -2.0 -0.4 16.1 18.3 -0.2 4.4 2.3 dibutyl ether 0.5 26.3 -1.4 -0.1 25.8 27.7 -0.6 5.4 2.7 1,2-dimethyoxyethane 0.8 -5.4 -4.4 0.7 -6.2 -1.0 -2.6 -0.1 -0.3 diethylene glycol dimethyl ether 1.3 -9.9 -6.5 1.2 -11.2 -3.3 -3.1 -0.5 -0.6 tetrahydrofuran 0.4 5.2 -2.0 0.3 4.7 7.1 -1.8 2.0 0.9 2-methyltetrahydrofuran 0.4 8.9 -1.9 0.2 8.5 10.8 -1.1 3.0 1.5 tetrahydropyran 0.5 9.0 -1.8 0.3 8.5 10.8 -1.3 2.9 1.4 Electronic Supplementary Material (ESI) for Chemical Science This journal is © The Royal Society of Chemistry 2013 4 Table S3.