Supporting information for:
Understanding the Solubility of Acetaminophen
in 1-n-Alkyl-3-methylimidazolium-Based Ionic
Liquids Using Molecular Simulation
Andrew S. Paluch,∗,† Tuanan C. Lourenço,‡ Fenglin Han,† and Luciano T.
Costa‡
Department of Chemical, Paper and Biomedical Engineering, Miami University, Oxford, Ohio
45056, USA, and Instituto de Química, Universidade Federal Fluminense - Outeiro de São João
Batista, s/n CEP:24020-141, Niterói-RJ, Brazil
E-mail: [email protected]
Phone: (513) 529-0784. Fax: (513) 529-0761
∗
To whom correspondence should be addressed
Miami University
‡
Universidade Federal Fluminense
†
S1
List of Figures
S1
Spatial distribution function projected in the xy plane showing the occurrence of
anions around the hydroxyl and amide groups from acetaminophen. . . . . . . . . S3
S2
Spatial distribution function projected in the xy plane of the anion and cation
center-of-mass around acetaminophen. . . . . . . . . . . . . . . . . . . . . . . . . S4
S3
Snapshot related to the acetaminophen (APAP)–anion interaction in the ionic liquid at 338.15 K and 1 bar. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . S5
List of Tables
S1
The computed (pure component) molar volume of the studied ionic liquids, water
and cyclohexane at 338.15 K and 1 bar, along with the computed dimensionless
residual chemical potential of acetaminophen infinitely dilute in each solvent. . . . S6
S2
The computed dimensionless residual chemical potential of benzene, phenol, and
acetanilide infinitely dilute in [BMIM]+ [CH3 CO2 ]− , water and cyclohexane at
338.15 K and 1 bar. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . S7
S3
The computed dimensionless residual chemical potential of benzene, phenol, acetanilide and acetaminophen infinitely dilute in water at 338.15 K and 1 bar using
the TIP4P, TIP4P-Ew and TIP4P/2005 water models. . . . . . . . . . . . . . . . . S7
S4
The computed dimensionless residual chemical potential of acetaminophen infinitely dilute in [BMIM]+ [PF6 ]− and [BMIM]+ [BF4 ]− at 338.15 K and 1 bar
using the ionic liquid force field of Zhong et al and Liu et al. . . . . . . . . . . . . S7
S2
Figure S1: Spatial distribution function projected in the xy plane showing the occurrence of anions
around the hydroxyl (OH, A) and amide (NH, B) groups from acetaminophen in the ionic liquid
[EMIM]+ [CH3 CO2 ]− at 338.15 K and 1 bar..
S3
Figure S2: Spatial distribution function projected in the xy plane of the anion (A) and cation (B)
center-of-mass around acetaminophen in the ionic liquid [EMIM]+ [CH3 CO2 ]− at 338.15 K and 1
bar. The occurrence is shown at the bottom of the figures.
S4
Figure S3: Snapshot related to the acetaminophen (APAP)–anion interaction in the ionic liquid
[EMIM]+ [CH3 CO2 ]− at 338.15 K and 1 bar.
S5
Table S1: The computed (pure component) molar volume of the studied ionic liquids, water
and cyclohexane at 338.15 K and 1 bar, along with the computed dimensionless residual
chemical potential of acetaminophen infinitely dilute in each solvent (1 =acetaminophen).
These are the calculations that form the basis of this work with the ionic liquids modeled
using the force field of Zhong et al and water modeled using TIP4P.
Solvent
[EMIM]+ [PF6 ]−
[EMIM]+ [TF2 N]−
[EMIM]+ [BF4 ]−
[EMIM]+ [CF3 SO3 ]−
[EMIM]+ [MeSO4 ]−
[EMIM]+ [CF3 CO2 ]−
[EMIM]+ [CH3 CO2 ]−
[BMIM]+ [PF6 ]−
[BMIM]+ [TF2 N]−
[BMIM]+ [BF4 ]−
[BMIM]+ [CF3 SO3 ]−
[BMIM]+ [MeSO4 ]−
[BMIM]+ [CF3 CO2 ]−
[BMIM]+ [CH3 CO2 ]−
[HMIM]+ [PF6 ]−
[HMIM]+ [TF2 N]−
[HMIM]+ [BF4 ]−
[HMIM]+ [CF3 SO3 ]−
[HMIM]+ [MeSO4 ]−
[HMIM]+ [CF3 CO2 ]−
[HMIM]+ [CH3 CO2 ]−
water
cyclohexane
v [cm3 /mol]
183.357±0.084
268.761±0.048
164.170±0.048
193.940±0.039
176.848±0.045
182.759±0.039
161.342±0.048
217.366±0.081
302.887±0.072
198.556±0.126
228.482±0.048
211.224±0.063
217.286±0.045
196.697±0.132
251.939±0.084
337.993±0.084
233.298±0.048
263.624±0.090
246.368±0.129
252.382±0.060
232.148±0.090
18.666±0.001
115.232±0.051
S6
βµres,∞
1,i
-25.17±0.16
-25.80±0.14
-26.59±0.11
-27.51±0.14
-28.94±0.23
-29.37±0.10
-34.20±0.18
-24.61±0.18
-24.81±0.15
-26.13±0.13
-26.88±0.17
-29.10±0.27
-29.59±0.11
-34.40±0.23
-25.10±0.21
-25.04±0.16
-21.64±0.17
-25.93±0.26
-29.62±0.24
-28.93±0.13
-34.18±0.23
-22.54±0.04
-11.69±0.14
Table S2: The computed dimensionless residual chemical potential of benzene, phenol, and
acetanilide infinitely dilute in [BMIM]+ [CH3 CO2 ]− , water and cyclohexane at 338.15 K and
1 bar. (1 ={benzene, phenol or acetanilide}) These are the calculations that form the basis
of this work with the ionic liquids modeled using the force field of Zhong et al and water
modeled using TIP4P.
Solvent
[BMIM]+ [CH3 CO2 ]−
water
cyclohexane
[BMIM]+ [CH3 CO2 ]−
water
cyclohexane
[BMIM]+ [CH3 CO2 ]−
water
cyclohexane
Solute
benzene
benzene
benzene
phenol
phenol
phenol
acetanilide
acetanilide
acetanilide
βµres,∞
1,i
-4.03±0.10
1.59±0.03
-6.02±0.11
-14.87±0.12
-8.24±0.03
-7.44±0.12
-21.64±0.18
-15.22±0.04
-10.03±0.14
Table S3: The computed dimensionless residual chemical potential of benzene, phenol, acetanilide and acetaminophen infinitely dilute in water at 338.15 K and 1 bar using the
TIP4P, TIP4P-Ew and TIP4P/2005 water models. (1 ={benzene, phenol, acetanilide or acetaminophen})
Water Model
TIP4P
TIP4P-Ew
TIP4P/2005
TIP4P
TIP4P-Ew
TIP4P/2005
TIP4P
TIP4P-Ew
TIP4P/2005
TIP4P
TIP4P-Ew
TIP4P/2005
Solute
benzene
benzene
benzene
phenol
phenol
phenol
acetanilide
acetanilide
acetanilide
acetaminophen
acetaminophen
acetaminophen
res,∞
βµ1,water
1.59±0.03
1.99±0.03
1.80±0.04
-8.24±0.03
-8.01±0.03
-8.27±0.03
-15.22±0.04
-14.84±0.05
-15.28±0.05
-22.54±0.04
-22.34±0.05
-22.73±0.06
Table S4: The computed dimensionless residual chemical potential of acetaminophen infinitely dilute in [BMIM]+ [PF6 ]− and [BMIM]+ [BF4 ]− at 338.15 K and 1 bar using the ionic
liquid force field of Zhong et al and Liu et al. (1 =acetaminophen)
IL
[BMIM]+ [PF6 ]−
[BMIM]+ [PF6 ]−
[BMIM]+ [BF4 ]−
[BMIM]+ [BF4 ]−
IL Force Field
Zhong et al
Liu et al
Zhong et al
Liu et al
S7
res,∞
βµ1,i
-24.61±0.18
-26.33±0.32
-26.13±0.13
-27.81±0.30