Article

pubs.acs.org/jced

Electrical Conductances of 1Butyl-3-propylimidazolium Bromide

and 1Butyl-3-propylbenzimidazolium Bromide in Water, Methanol,
and Acetonitrile at (308, 313, and 318) K at 0.1 MPa
Sumanta Gupta, Amritendu Chatterjee, Sajal Das, and Basudeb Basu
Department of Chemistry, North Bengal University, Darjeeling 734013, India

Bijan Das*,
Department of Chemistry & Biochemistry, Presidency University, 86/1 College Street, Kolkata 700 073, India
ABSTRACT: Two ionic liquids (ILs), 1-butyl-3-propyl imidazolium bromide ([BPim][Br]) and 1-butyl-3-propyl benzimidazolium
bromide ([BPbim][Br]), have been synthesized from their appropriate imidazole and benzimidazole precursors and were characterized by NMR spectroscopic technique. Their electrical
conductances have been measured as a function of their concentrations in water, methanol, and acetonitrile at three dierent temperatures. The limiting molar conductances (0), the association
constants (KA), and the values of the association diameters (R)
of these ILs have been obtained by analysis of the conductance
data using the Fuoss conductance equation. These ILs have been
found to remain unassociated in water and methanol, whereas
these exhibit slight ionic association in acetonitrile within the
investigated temperature range. The temperature elevation causes an increase in their limiting molar conductances in the three
solvents under investigation. The IL cations [BPim]+ and [BPbim]+ exist as unsolvated species in aqueous solutions, whereas
substantial solvation was noticed for the [BPim]+ ion in methanol and acetonitrile solutions.

INTRODUCTION

EXPERIMENTAL SECTION
Chemicals. Acetonitrile (purity: 99 %) was purchased from
E. Merck, India; it was puried by distillation with P2O5 followed
by redistillation over CaH2. Methanol (purity: 99.9 %) was
procured from Acros Organics and was distilled three times.
Deionized triply distilled water was used for the preparation of
solutions; its specic conductivity was of the order of 0.1 mSm1
at 308 K. The densities (0) and the viscosity coecients (0) of
the solvents thus puried are shown in Table 1, and these
properties agree well with those reported in the literature.2024
The relative permittivities () of these solvents were obtained
from the literature,2023 and these are also listed in Table 1.
The relative permittivity of methanol at 313 K is not available
in the literature, and this was obtained from an interpolation
of the available experimental relative permittivity values in the
temperature range (278 to 328) K.21 1-Bromopropane (purity:
98.5 %), 1-bromobutane (purity: 98 %), and benzimidazole
(purity: 99.5 %) were purchased from Loba Chemie, India, and
imidazole (purity: 99 %) was purchased from SRL, India; these
were used without further purication.

Ionic liquids (ILs) constitute a group of molten organic electrolytes whose chemical and physical properties could be conveniently
engineered by judicious choice of their anions, cations, and the
substituents. They possess specic properties, for example, negligible
vapor pressures, noninammability, good thermal stability under
ordinary conditions, and outstanding catalytic properties, and
above all they oer excellent solubility for inorganic and organic
compounds.14 Recent years have, therefore, witnessed an upsurge
of interest in ILs in the eld of scientic research opened up by the
possibility of their applications in novel eco-friendly and benign
industrial processes.511 Plenty of physicochemical investigations
have, so far, been performed on pure ILs as well as on their
mixtures with molecular solvents.1215 However, only in a limited
number of cases, the innite dilution molar properties1619 were
obtained despite their importance in understanding the ionion
and ionsolvent interactions and the possibility of prediction of
ILs in specic applications such as IL-based chemical reactions.
This article reports the electrical conductances measured for
1-butyl-3-propyl imidazolium bromide ([BPim][Br]) and 1-butyl3-propyl benzimidazolium bromide ([BPbim][Br]) dissolved in
water, methanol, and acetonitrile at (308, 313, and 318) K at
0.1 MPa as a function of concentration of these ILs with a view
to unravel their association and solvation behavior.
2012 American Chemical Society

Received: December 20, 2011

Accepted: November 29, 2012
Published: December 7, 2012
1

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method to that used for synthesizing IL 1, with imidazole (instead

of benzimiazole) as the starting material. This was characterized by
NMR spectroscopy [1H NMR (300 M Hz, CDCl3) (ppm):
10.30 (s, 1H), 7.64 (s, 1H), 7.61 (s, 1H), 4.404.33 (m, 4H),
2.021.87 (m, 4H), 1.421.32 (m, 2H), 1.010.92 (m, 6H); 13C
NMR (75 M Hz, CDCl3) (ppm): 137.27, 123.38, 123.26, 52.09,
50.47, 32.94, 24.46, 20.16, 14.23, 11.46]. The structure of this ionic
liquid is shown in Figure 1.
Electrical Conductance Measurements. Electrical conductances were measured on a calibrated Orion 3-Star conductivity meter at 2 kHz using a cell (dip-type) having a cell
constant of 115 m1. Uncertainties of the measurements were
always within 0.01 %. The conductivity cell was calibrated
following the methods described in the literature27,28 by using
KCl (aq) solution. All measurements were carried out in a
water bath controlled to 0.05 K. The necessary correction for
the solvent specic conductance was done. Details of the experimental method are available in the literature.29 The IL solutions
were prepared on molality basis, and the molalities of the solutions
were converted into molarities by using their densities. The
reproducibility of the experimental data was checked by repeating
the measurements with dierent stock solutions.
Density Measurements. Density measurements were
carried out on an Anton Paar DMA-4500 M digital precision
densimeter. The precision of the density measurements was
3105 gcm3. Calibration of the densimeter was done at each
temperature using dry air under ambient pressure and deionized
triply distilled water.
Viscosity Measurements. The kinematic viscosities ()
were determined with an Ubbelohde viscosimeter. The viscosimeter
was kept in a water bath maintained within 0.05 K of the
experimental temperatures. The absolute viscosities () have
then been calculated from the kinematic viscosity values by
using the density values. In each case, an average of triplicate
measurements was taken into account.

Table 1. Physical Properties of Water, Methanol, and

Acetonitrile at (308, 313, and 318) K at 0.1 MPaa
0/gcm3
T/K

this work

308
313
318

0.99407
0.99221
0.99024

308
313
318

0.77718
0.77250
0.76770

308

0.76564

313
318

0.75970
0.75501

0/mPas
lit.

this work

Water
0.9940622
0.7194
0.9922422
0.6533
0.9902422
0.5966
Methanol
0.7772023
0.4747
0.4440
0.7677023
0.4185
Acetonitrile
0.7658124
0.3125
0.766225
0.7656026
0.3042
0.7527124
0.2903
0.755925

lit.

0.719422
0.653122
0.596322

74.8222
73.1522
71.5122

0.474223

30.7423
29.81b
28.9223

0.417423
0.31424

24

0.293
0.28925

34.124
34.5425
33.8525
33.1225

a
The uncertainty u is u(T) = 0.05 K. Combined expanded
uncertainties are Uc(0) = 0.00003 gcm3 and Uc(0) = 0.005
mPas (level of condence = 0.95). bObtained from interpolation of
the literature values from ref 21 (please see text).

Synthesis of 1-Butyl-3-propylbenzimidazolium Bromide.25 To a round-bottomed ask containing benzimidazole

(5.9 g, 50 mmol) in acetonitrile (30 mL) were added KOH
(5.6 g, 100 mmol) and 1-bromobutane (7 g, 51 mmol). This
mixture, after reuxing for about 4 h, was cooled down to
ambient temperature. The solvent was then evaporated under
vacuum; 30 mL of dichloromethane was added to it, and
potassium bromide was removed by washing the material with
water using a separatory funnel. The nonaqueous layer was
dehydrated with Na2SO4, which on evaporation left behind the
crude product (1-butyl-benzimidazole). To the crude material
taken in a dry ask containing dry ethanol (20 mL) was added
1.1 equivalent amount of propyl bromide. The content of the
ask was then reuxed for 24 h under nitrogen atmosphere, and
after cooling down to ambient temperature, evaporation of the
solvent was done under vacuum. The crude material, 1-butyl-3propyl benzimidazolium bromide, was nally recrystallized
from ethanol in the form of a white solid (1). This was characterized by NMR spectroscopy [1H NMR (500 M Hz, CDCl3)
(ppm): 11.32 (s, 1H), 7.667.19 (m, 4H), 4.56 (t, 2H, J =
12.4), 4.53 (t, 2H, J = 12.3), 2.061.91 (m, 4H), 1.411.34
(m, 2H), 0.990.88 (m, 6H); 13C NMR (75 M Hz, CDCl3)
(ppm): 143.74, 132.24, 132.20, 128.05, 114.08, 114.04, 49.90,
48.35, 32.26, 23.75, 20.68, 14.39, 11.90]. The structure of this
ionic liquid is depicted in Figure 1.

RESULTS AND DISCUSSION

Table 2 lists the molar conductivity values obtained experimentally as functions of the molality (m) of the IL solutions at
(308, 313, and 318) K at 0.1 MPa. These were analyzed by
using the Fuoss conductance equation.30,31 A given set of conductance data (cj, j; j = 1, ..., n) can provide three parameters,
namely, the limiting molar conductivity (0), the equilibrium
constant for ionic association (KA), and the distance of the
closest approach of ions (R). For a given data set these three
parameters were obtained by an iterative solution of the following
set of equations:
= p[0(1 + RX + EL]

(1)

p = 1 (1 )

(2)

KA = (1 )/c 2f 2

(3)

ln f =

Figure 1. Structures of the ionic liquids -1-butyl-3-propylbenzimidazolium bromide (1) and 1-butyl-3-propylimidazolium bromide (2).

k
2(1 + kR )

e2
kBT

(4)

(5)

KA = KR (1 + KS)

(6)

where RX is the relaxation eld eect, EL is the electrophoretic

countercurrent, is the fraction of unpaired ions, is the

26

Synthesis of 1-Butyl-3-propylimidazolium Bromide.

Synthesis of this IL (2) was accomplished by following a similar

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Table 2. Molalilty Dependence of the Molar Conductances of 1-Butyl-3-propylimidazolium Bromide and 1-Butyl-3propylbenzimidazolium Bromide in Water, Methanol, and Acetonitrile at (308, 313, and 318) K at 0.1 MPaa
104m/molkg1

T = 308 K

T = 313 K

T = 318 K

/Scm2mol1

/Scm2mol1

/Scm2mol1

104m/molkg1

1-Butyl-3-propylimidazolium Bromide in Water

99.60
108.00
117.70
100.84
109.40
118.98
103.04
111.65
120.94
106.50
115.18
124.01
109.50
118.24
126.69
112.12
120.91
129.05
114.41
123.20
131.16
116.42
125.31
133.05
118.18
127.12
134.74
119.72
128.72
136.25
121.06
130.13
137.60
122.24
131.36
138.70
1-Butyl-3-propylimidazolium Bromide in Methanol
1001.93
52.38
55.40
59.23
901.74
53.04
56.11
60.16
766.46
53.72
57.03
61.23
574.86
54.68
58.32
62.57
431.14
55.61
59.36
63.71
323.38
56.68
60.52
64.91
242.51
57.92
61.85
66.27
181.88
59.32
63.33
67.81
136.42
60.83
64.93
69.46
102.31
62.39
66.58
71.19
76.73
63.95
68.15
72.90
57.55
65.46
74.80
1-Butyl-3-propylimidazolium Bromide in Acetonitrile
998.72
59.20
61.99
64.35
898.24
61.24
63.93
66.48
762.82
64.33
67.01
69.68
656.05
67.07
69.56
72.55
571.39
69.44
72.22
75.23
487.52
74.67
78.07
428.13
74.24
77.24
80.54
320.88
78.83
82.13
85.95
1-Butyl-3-propylimidazolium Bromide in Acetonitrile
274.96
81.23
240.52
83.25
86.91
91.14
180.33
87.51
91.55
96.27
135.20
91.60
96.04
101.28
101.38
95.50
100.75
106.30
1-Butyl-3-propylbenzimidazolium Bromide in Water
1330.01
95.87
102.58
1200.00
97.37
103.93

T = 313 K

T = 318 K

/Scm2mol1

/Scm2mol1

1-Butyl-3-propylbenzimidazolium Bromide in Water

1030.11
89.21
99.31
106.06
924.81
90.76
830.46
92.06
788.15
92.62
101.90
108.92
588.31
94.90
104.02
111.25
439.66
96.77
105.66
113.27
328.87
98.07
107.06
114.95
246.17
99.14
108.29
116.56
184.36
100.06
109.39
117.88
138.11
100.90
110.38
119.08
103.49
101.65
111.26
120.20
77.57
102.35
1-Butyl-3-propylbenzimidazolium Bromide in Methanol
1012.50
51.41
55.43
61.11
910.23
53.07
57.28
62.91
772.52
54.88
59.29
64.81
578.14
56.82
61.37
66.76
432.94
58.04
62.63
67.94
324.32
59.06
63.67
68.96
243.02
60.09
64.72
70.02
182.15
61.20
65.87
71.23
136.53
62.41
67.12
72.57
102.37
63.80
68.46
74.00
76.75
64.98
69.83
75.49
57.55
66.27
71.32
77.17
1-Butyl-3-propylbenzimidazolium Bromide in Acetonitrile
999.54
70.05
73.20
76.63
898.29
72.99
76.19
79.74
762.02
77.40
80.55
84.43
1-Butyl-3-propylbenzimidazolium Bromide in Acetonitrile
569.99
84.76
88.04
92.53
426.63
91.79
95.37
100.44
319.48
98.55
102.39
108.20
239.36
105.06
109.39
115.81
179.35
111.34
116.13
123.22
134.48
117.30
122.62
130.37
100.77
123.03
128.73
137.18
75.55
128.28
134.66
143.35
56.65
133.04
140.64

1000.40
898.74
762.10
569.63
426.16
319.02
238.91
178.98
134.14
100.54
75.36
56.51

T = 308 K
/Scm2mol1

Standard uncertainties u are u(T) = 0.05 K and u(m) = 0.00002 molkg1, and the combined expanded uncertainty Uc is Uc() = 0.03 Scm2mol1 (level
of condence 0.95).

Following Fuoss,30 calculations were performed over a range

of R values to nd the 0 and KA values minimizing the
standard deviations, ,

fraction of contact pairs, KA is the overall pairing constant

evaluated from the association constants of contact pairs (KS)
of solvent-separated pairs (KR), is the relative permittivity of
the solvent, e is the electronic charge, kB is the Boltzmann
constant, k1 is the radius of the ion atmosphere, c is the
molarity of the solution, f is the activity coecient, T is the
temperature in absolute scale, and is twice the Bjerrum
distance. The initial values of 0 for the iteration procedure
have been obtained by extrapolating the data according to
Shedlovsky and Fuoss.32

= [ [j(calcd) j(obsd)]2 /(n 2)]1/2

(7)

of the ts; the value of R which ts the experimental data best

was, therefore, identied as the minimum of a vs R prole.
The 0, KA, and R values thus derived from the conductance
data are recorded in Table 3.
3

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Table 3. Derived Conductivity Parameters for 1-Butyl-3-propylimidazolium Bromide and 1-Butyl-3-propylbenzimidazolium

Bromide in Water, Methanol, and Acetonitrile at (308, 313, and 318) K at 0.1 MPa
IL

T/K

0/Scm2mol1

KA/dm3mol1

R/

2.87
2.57
1.73
0.74
1.16
1.50

0.01
0.02
0.01
0.01
0.01
0.01

8.1
8.0
7.7
12.6
11.4
10.1

0.05
0.06
0.03
0.04
0.02
0.03

2.31
3.06
3.09
0.93
0.58
0.18

0.02
0.05
0.06
0.05
0.04
0.06

4.6
4.8
4.9
5.8
5.8
5.6

0.02
0.04
0.05
0.04
0.04
0.06

32.83
37.61
42.97
49.25
54.76
60.33

0.09
0.12
0.08
0.09
0.09
0.01

7.7
7.2
7.2
10.0
9.7
10.0

0.02
0.02
0.02
0.02
0.02
0.01

Water
[BPim][Br]

[BPbim][Br]

[BPim][Br]

[BPbim][Br]

[BPim][Br]

[BPbim][Br]

308
313
318
308
313
318

130.22
139.89
147.50
108.83
118.87
129.03

308
313
318
308
313
318

79.35
84.75
90.61
79.21
85.09
92.03

308
313
318
308
313
318

128.10
136.41
145.89
166.92
177.04
190.64

0.03
0.05
0.02
0.03
0.02
0.03
Methanol
0.01
0.03
0.04
0.02
0.02
0.04
Acetonitrile
0.04
0.08
0.05
0.05
0.05
0.01

The representative plots (Figures 2 to 4) show the dependence

of the experimental on the IL molality. Also included in these
gures are the calculated proles in accordance with eqs 1 to 6.

Figure 3. Variation of molar conductivity of 1-butyl-3-propylimidazolium bromide as a function of molality in methanol at dierent
temperatures at 0.1 MPa. The symbols represent the experimental
points, whereas the lines represent the calculations according to eqs 1
through 6. , 318 K; , 313 K; , 308 K.

Figure 2. Variation of molar conductivity of 1-butyl-3-propylimidazolium bromide as a function of molality in water at dierent
temperatures at 0.1 MPa. The symbols represent the experimental
points, whereas the lines represent the calculations according to eqs 1
through 6. , 318 K; , 313 K; , 308 K.

also change in the same order as the limiting equivalent conductivities of the ILs as a whole. It is now well-established33
that some ions exist as bare species (unsolvated) in solution
with sizes being equal to their crystallographic sizes, whereas
others are solvated with a concomitant increase in their actual
sizes in solution. The order of variation of the limiting ionic
equivalent conductivities should, thus, point out the relative
ionic solvodynamic dimensions and hence provide information
on their solvation behavior in solutions.
The ionic mobilities of the IL cations in water decrease in the
order: [BPim]+ > [BPbim]+. This indicates that the larger IL
cation is less mobile than the smaller one in aqueous solution.
This is possible only if the ions remain unsolvated in water; had
these IL cations been hydrated, the smaller ion [BPim]+ with a
higher charge density on its surface would have been more
hydrated compared to the bigger [BPbim]+ ion (with smaller
surface charge density), and hence their ionic mobilities should

The 0 values for the two ILs investigated are found to

increase with temperature, and these could be described by the
following linear relationship:
0 = a0 + a1(308.15 T )

(8)

and the values of the coecients of eq 8, together with the

correlation coecients (r), have been listed in Table 4.
An inspection of the variation of the limiting ionic equivalent
conductivities of the IL cations in the investigated solvents
could provide an important clue to their solvation in these
media. Since the anion is common to both the ILs, the limiting
ionic equivalent conductivities of the IL cations, according to
the Kohlrauschs law of independent migration of ions, would
4

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other hand, the fractions of unpaired ions are found to be in the

range of 0.470.86 within the investigated concentration and
temperature ranges; this observation demonstrates that a substantial proportion of these ILs are associated and exist as ion
pairs in acetonitrile. Further, the extent of ion association in
acetonitrile increases as the temperature is elevated (cf. Table 3).
Now, an increase in temperature causes ion desolvation as well
as an attenuation of the product of the relative permittivity and
the absolute temperature (T) for this medium. Desolvation
promotes ion association, and a decrease in the T value also
enhances the value of the association constant according to eqs
3 to 5. Hence both these eects might have been contributed to
the increase in the KA values with temperature in acetonitrile.
The existence of free ions for these two ILs in water might be
attributed to the high values of the relative permittivity of the
medium (ranging from 71.51 to 74.82 over the investigated
range of temperature), thus promoting the dissociation of these
electrolytes.
Since the relative permittivities of methanol and acetonitrile
are not very much dierent, one expects close correspondence
in the KA values of these ILs in these solvent media if Coulombic
forces are only responsible for ionic association governed by the
relative permittivities of the media. The large dierences between
the KA values of the ILs in methanol and acetonitrile indicate that
the association/dissociation behavior of these ILs in methanol and
acetonitrile could not be accounted for only on the basis of the
relative permittivities of these two solvents. Non-Coulombic forces
might, therefore, play a decisive role in the ionic association
phenomena in acetonitrile. Further studies in this direction are,
therefore, necessary.

Figure 4. Variation of molar conductivity of 1-butyl-3-propylbenzimidazolium bromide as a function of molality in acetonitrile at dierent
temperatures at 0.1 MPa. The symbols represent the experimental
points, whereas the lines represent the calculations according to eqs 1
through 6. , 318 K; , 313 K; , 308 K.

Table 4. Coecients of Equation 8

IL
[BPim][Br]
[BPbim][Br]
[BPim][Br]
[BPbim][Br]
[BPim][Br]
[BPbim][Br]

a0
Water
130.56
108.81
Methanol
79.27
79.03
Acetonitrile
127.91
166.34

a1

r2

1.7280
2.0200

0.9953
0.9996

1.1260
1.2820

0.9994
0.9977

1.7790
2.3720

0.9986
0.9929

CONCLUSIONS
Two ionic liquids, 1-butyl-3-propyl imidazolium bromide
([BPim][Br]) and 1-butyl-3-propyl benzimidazolium bromide
([BPbim][Br]), have been synthesized respectively from their
appropriate imidazole and benzimidazole precursors and characterized by NMR spectroscopic technique. The electrical conductances of these two ionic liquids were measured as functions
of their concentrations in water, methanol, and acetonitrile at
dierent temperatures. Analyses of the conductance data on the
basis of the Fuoss conductance equation provided important
insight into the ion association and solvation behavior on the
investigated ionic liquid solutions.

have followed an opposite order. This observation thus suggests

that the IL ions [BPim]+ and [BPbim]+ exist as unsolvated
species in aqueous solutions.
The ionic mobilities of the IL cations [BPim]+ and [BPbim]+
in methanol are approximately the same. This suggests that the
solvodynamic dimensions of these IL cations in methanol are
similar. Thus it can be inferred that at least the smaller cation
[BPim]+ is solvated in methanol.
A comparison of the trend in the IL cationic mobilities in
acetonitrile with their bare sizes indicates that the bigger the
bare size of cation, the more mobile it would be. Therefore, the
solvodynamic dimensions of the cations in acetonitrile solution
decrease in the order: [BPbim]+ > [BPim]+. Thus there is apparent
signicant solvation of the [BPim]+ ion by the acetonitrile
molecules so that it turned into a bigger solvodynamic entity
than the [BPbim]+ ion.
The present study, however, does not rule out the possibility
of solvation of the [BPbim]+ ion in methanol and acetontrile
solutions, although weaker solvation is expected for this ion
compared to [BPim]+ ion since the former with a bigger size
would possess a smaller surface charge density compared to the
latter.
The association constants of these two ILs in the three media
investigated are listed in Table 3. Now, the fractions of
unpaired ions () can be obtained from the KA values using eqs
3 to 5. The fractions of unpaired ions are found to be in the
range of 0.871.00 for the two ILs in water and methanol
within the investigated concentration and temperature ranges
indicating that a preponderant proportion of these ILs remain
in the form of free ions. For these ILs in acetonitrile, on the

AUTHOR INFORMATION

Corresponding Author

*E-mail: bijan_dasus@yahoo.com.
Notes

Previous address: Department of Chemistry, North Bengal

University, Darjeeling 734013, India.
Funding

Financial assistance by the Department of Science and Technology,

New Delhi, Government of India (SR/S1/PC-67/2010 and SR/
FT/CS-017/2010) and the Department of Chemistry, North
Bengal University are gratefully acknowledged.
Notes

The authors declare no competing nancial interest.

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