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. 2023 Jul 12;8(29):26533–26547. doi: 10.1021/acsomega.3c03326

Table 1. Predicted Activity Coefficients at Infinite Dilution (γi∞) of the Targeted Monosaccharides in the 212 DES Constituents at 298.2 K and 1.01 Bar.

# constituent ln(γ∞Fru) ln(γ∞Glu) # constituent ln(γ∞Fru) ln(γ∞Glu)
  hydrogen bond acceptors (HBAs)     D17 hydroquinone38 –3.534 –1.812
A1 ammonium chloride –76.380 –76.020 D18 maleic acid39 –3.165 –2.097
A2 ammonium bromide –68.513 –66.997 D19 urea40 –1.935 –3.001
A3 tetramethylammonium chloride –15.282 –17.604 D20 phenol41 –3.446 –1.118
A4 carnitine42 –13.710 –16.525 D21 3-salicylic acid43 –2.978 –1.486
A5 tetramethyl phosphonium chloride –13.725 –16.151 D22 tartaric acid44 –2.672 –1.692
A6 betaine42 –12.899 –15.610 D23 malonic acid45 –2.565 –1.765
A7 tetraethylammonium chloride –12.540 –15.047 D24 lidocaine46 –1.549 –2.761
A8 tetraethylphosphonium chloride –12.514 –15.030 D25 diethylene glycol47 –1.566 –2.727
A9 choline chloride8 –11.912 –14.189 D26 methanol48 –1.460 –2.700
A10 tetramethylammonium bromide –11.796 –13.654 D27 formic acid49 –2.446 –1.601
A11 tetrapropylammonium chloride –11.001 –13.526 D28 diethanolamine50 –1.364 –2.611
A12 tetrapropylphosphonium chloride –10.838 –13.354 D29 1,4-butanediol19 –1.152 –2.522
A13 benzyltriethylammonium chloride51 –10.543 –12.955 D30 2-salicylic acid52 –2.637 –0.669
A14 benzyltriethylphosphonium chloride51 –10.466 –12.882 D31 1,3-propanediol53 –0.985 –2.150
A15 dimethylethylethanolammonium chloride –10.472 –12.833 D32 3-cresol50 –2.619 –0.479
A16 diethylethanolammonium chloride –10.393 –12.849 D33 bisphenol Z54 –2.499 –0.452
A17 tetrabutylammonium chloride55 –10.244 –12.752 D34 2-methylpentanediol56 –0.793 –2.142
A18 tetrabutylphosphonium chloride57 –10.065 –12.566 D35 4-phenyl phenol38 –2.741 –0.058
A19 tetramethyl phosphonium bromide –10.284 –12.182 D36 ethanol58 –0.785 –1.948
A20 tetrapentylammonium chloride –9.795 –12.289 D37 4-cresol50 –2.400 –0.157
A21 benzyl trimethylammonium chloride –9.698 –12.040 D38 2-cresol50 –2.510 –0.033
A22 benzyl trimethyl phosphonium chloride –9.689 –12.039 D39 sesamol43 –2.121 –0.188
A23 tetrapentylphosphonium chloride –9.510 –11.995 D40 ethylene glycol53 –0.649 –1.644
A24 acetylcholine chloride –9.435 –11.704 D41 malic acid44 –1.431 –0.646
A25 tetrahexylammonium chloride –9.248 –11.730 D42 4-ethylphenol59 –2.183 0.121
A26 1-butyl-3-methylimidazolium chloride52 –9.183 –11.654 D43 N-methyl diethanolamine60 –0.465 –1.366
A27 butyltriphenylphosphonium chloride –9.146 –11.499 D44 propylene glycol61 –0.442 –1.343
A28 tetra hexyl phosphonium chloride –9.062 –11.535 D45 4-cyanophenol38 –1.474 0.042
A29 tetraheptylammonium chloride62 –8.826 –11.297 D46 acetic acid63 –0.884 –0.515
A30 allyl triphenylphosphonium chloride –8.826 –11.145 D47 4-propyl phenol59 –1.876 0.484
A31 methyl triphenylphosphonium chloride –8.743 –11.058 D48 xylitol40 –0.286 –0.903
A32 tetraheptylphosphonium chloride62 –8.624 –11.085 D49 1,6-hexanediol19 –0.091 –1.093
A33 tetraethylammonium bromide –8.908 –10.794 D50 glycerol64 –0.211 –0.950
A34 tetraethylphosphonium bromide –8.849 –10.713 D51 thiourea65 –1.073 –0.050
A35 tetraoctylammonium chloride66 –8.506 –10.968 D52 ascorbic acid67 –0.806 –0.221
A36 methyl triphenyl ammonium chloride –8.546 –10.866 D53 1,2-butanediol53 –0.065 –0.831
A37 1-hexyl-3-methylimidazolium chloride52 –8.420 –10.879 D54 lactic acid68 –0.585 –0.216
A38 choline bromide –8.715 –10.581 D55 levulinic acid69 –0.426 –0.363
A39 methyltrioctylphosphonium chloride70 –8.418 –10.870 D56 polyethylene glycol 20071 –0.085 –0.695
A40 benzyltriphenylphosphonium chloride72 –8.464 –10.750 D57 thymol56 –1.754 0.998
A41 benzyltriphenylammonium chloride72 –8.413 –10.698 D58 1-propanol53 0.096 –0.850
A42 methyltrioctylammonium chloride70 –8.299 –10.753 D59 propionic acid73 –0.570 –0.028
A43 tetraoctylphosphonium chloride66 –8.298 –10.749 D60 glycolic acid74 –0.414 –0.157
A44 hexadecyltrimethylphosphonium chloride –7.831 –10.248 D61 mequinol59 –1.143 0.602
A45 dodecyldimethylbenzylphosphonium chloride75 –7.678 –10.029 D62 1,2-decanediol76 0.348 –0.865
A46 dodecyldimethylbenzylammonium chloride75 –7.595 –9.948 D63 maltitol40 0.214 –0.730
A47 tetrapropylammonium bromide –7.586 –9.414 D64 maltose61 –0.034 –0.450
A48 hexadecyltrimethylammonium chloride –7.304 –9.695 D65 mandelic acid73 –0.780 0.442
A49 tetrapropylphosphonium bromide –7.456 –9.272 D66 pyruvic acid68 –0.804 0.570
A50 dimethylethylethanolammonium bromide –7.395 –9.289 D67 1,8-octanediol77 0.355 –0.572
A51 diethylethanolammonium bromide –7.048 –8.952 D68 diclofenac78 –1.321 1.212
A52 benzyltriethylammonium bromide51 –7.107 –8.871 D69 sorbitol40 0.087 –0.171
A53 benzyltriethylphosphonium bromide51 –7.054 –8.806 D70 1-butanol53 0.475 –0.450
A54 tetrabutylammonium bromide55 –6.864 –8.647 D71 atropine76 0.354 –0.299
A55 tetrabutylphosphonium bromide57 –6.721 –8.495 D72 benzoic acid52 –0.619 0.766
A56 benzethonium chloride –6.482 –8.613 D73 cyclohexanol53 0.584 –0.424
A57 benzyl trimethyl phosphonium bromide –6.602 –8.363 D74 trioctylphosphine79 1.058 –0.725
A58 benzyl trimethylammonium bromide –6.536 –8.305 D75 phenylacetic acid73 –0.456 0.848
A59 tetrapentylammonium bromide –6.385 –8.137 D76 trifluoroacetamide80 –0.323 0.832
A60 acetylcholine bromide –6.370 –8.139 D77 1,10-decanediol75 0.800 –0.043
A61 tetrapentylphosphonium bromide –6.168 –7.912 D78 anise alcohol81 0.454 0.371
A62 1-butyl-3-methylimidazolium bromide52 –5.904 –7.755 D79 sobrerol82 0.655 0.248
A63 tetrahexylammonium bromide –5.843 –7.574 D80 ethyl paraben83 –0.026 1.132
A64 butyltriphenylphosphonium bromide –5.757 –7.408 D81 allantoic acid 0.808 0.575
A65 tetrahexylphosphonium bromide –5.703 –7.425 D82 2-phenylethanol84 0.716 0.675
A66 allyl triphenylphosphonium bromide –5.544 –7.178 D83 trimethyl-1,3-pentanediol85 1.073 0.340
A67 methyl triphenylphosphonium bromide86 –5.510 –7.151 D84 camphor82 0.982 0.627
A68 tetraheptylammonium bromide62 –5.407 –7.119 D85 hexanoic acid87 0.529 1.303
A69 1-hexyl-3-methylimidazolium bromide52 –5.271 –7.079 D86 phenyl salicylate88 0.562 1.450
A70 methyl triphenyl ammonium bromide –5.336 –6.992 D87 1-hexanol53 1.421 0.688
A71 tetraheptylphosphonium bromide62 –5.264 –6.967 D88 coumarin76 1.013 1.257
A72 methyltrioctylphosphonium bromide70 –5.163 –6.868 D89 ketoprofen89 0.613 1.660
A73 benzyltriphenylphosphonium bromide72 –5.193 –6.785 D90 heptanoic acid90 0.779 1.659
A74 benzyltriphenylammonium bromide72 –5.155 –6.752 D91 ibuprofen91 0.438 2.069
A75 methyltrioctylammonium bromide70 –5.080 –6.788 D92 1-heptanol90 1.748 1.082
A76 tetraoctylammonium bromide66 –5.053 –6.750 D93 water92−94 2.128 0.856
A77 tetraoctylphosphonium bromide66 –4.910 –6.598 D94 octanoic acid95 1.026 1.969
A78 hexadecyltrimethylphosphonium bromide –4.889 –6.591 D95 alpha-terpineol96 1.755 1.272
A79 dodecyldimethylbenzylphosphonium bromide75 –4.798 –6.443 D96 glycine97 2.830 0.403
A80 dodecyldimethylbenzylammonium bromide75 –4.697 –6.347 D97 nonanoic acid95 1.228 2.248
A81 hexadecyltrimethylammonium bromide –4.490 –6.181 D98 2-dodecanol72 2.208 1.273
A82 beta-alanine18 –4.068 –6.547 D99 1-octanol53 2.045 1.444
A83 benzethonium bromide –3.859 –5.310 D100 10-undecenoic acid98 1.161 2.371
A84 butylammonium chloride –2.788 –5.550 D101 carvacrol99 0.807 2.771
A85 ethyl ammonium chloride –2.723 –5.591 D102 decanoic acid70 1.444 2.496
A86 propylammonium chloride –2.483 –5.312 D103 1-nonanol100 2.286 1.731
A87 butylammonium bromide –0.806 –2.874 D104 menthol101 2.302 1.789
A88 propylammonium bromide –0.173 –2.333 D105 undecanoic acid102 1.595 2.748
A89 ethyl ammonium bromide 0.563 –1.744 D106 1-decanol53 2.513 2.027
  hydrogen bond donors (HBDs)     D107 ricinoleic acid103 2.185 2.385
D1 perfluorodecanoic acid104 –11.536 –9.043 D108 dodecanoic acid68 1.791 2.970
D2 trioctylphosphine oxide79 –6.611 –9.218 D109 borneol82 2.463 2.308
D3 hexafluoroisopropanol42 –7.599 –4.814 D110 1-undecanol105 2.697 2.239
D4 dodecylmethylsulfoxide54 –5.123 –7.257 D111 carveol76 1.712 3.331
D5 oxalic acid61 –6.874 –5.407 D112 1,3-dihexylthiourea54 2.192 3.124
D6 5-sulfosalicylic acid106 –6.455 –5.022 D113 1-dodecanol53 2.911 2.527
D7 ethanolamine50 –4.586 –6.403 D114 tetradecanoic acid107 2.075 3.367
D8 polyethylene glycol 40071 –4.632 –6.327 D115 oleic acid91 2.240 3.731
D9 3,5-di-tert-butylcatechol54 –6.254 –3.195 D116 hexadecenoic acid108 2.326 3.691
D10 p-toluenesulfonic acid109 –4.734 –2.832 D117 1-tetradecanol53 3.200 2.869
D11 gallic acid110 –4.497 –3.023 D118 octadecanoic acid107 2.560 4.012
D12 4-chlorophenol59 –4.711 –2.094 D119 1-hexadecanol54 3.456 3.188
D13 citric acid40 –3.926 –2.866 D120 oleyl alcohol111 3.492 3.504
D14 1-naphthol76 –4.768 –1.824 D121 triphenyl phosphate79 3.737 5.175
D15 triethylene glycol112 –2.517 –3.766 D122 benzoyltrifluoroacetone79 3.775 6.082
D16 triethanolamine50 –2.140 –3.543 D123 thenoyltrifluoroacetone79 3.236 5.180