3-(1-Methyl-3-imidazolio)propane­sulfonate: a precursor to a Brønsted acid ionic liquid

Reichert, W.M.; Trulove, P.C.; De Long, H.C.

doi:10.1107/S1600536810004344

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o591

doi:10.1107/S1600536810004344

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3-(1-Methyl-3-imidazolio)propanesulfonate: a precursor to a Brønsted acid ionic liquid

W. Matthew Reichert,^a Paul C. Trulove ^a ^* and Hugh C. De Long ^b

^aDepartment of Chemistry, US Naval Academy, 572 M. Holloway Road, Annapolis, Maryland 21402, USA, and ^bAir Force Office of Scientific Research, 4015 Wilson Boulevard, Arlington, Virginia 22203, USA
^*Correspondence e-mail: trulove@usna.edu

(Received 24 November 2009; accepted 3 February 2010; online 13 February 2010)

The title compound, C₇H₁₂N₂O₃S, is a zwitterion precursor to a Brønsted acid ionic liquid with potential as an acid catalyst. The C—N—C—C torsion angle of 100.05 (8)° allows the positively charged imidazolium head group and the negatively charged sulfonate group to interact with neighboring zwitterions, forming a C—H⋯O hydrogen-bonding network; the shortest among these interactions is 2.9512 (9) Å. The C—H⋯O interactions can be described by graph-set notation as two R²₂(16) and one R²₂(5) hydrogen-bonded rings.

Related literature

For the use of functionalized ionic liquids (ILs) as Brønsted acid catalysts for organic reactions, see: Cole et al. (2002 ); Yoshizawa et al. (2001 ). The local structure of ILs is often conserved on transition from the solid state to the liquid state, see: Henderson et al. (2007 ); Reichert et al. (2007 ); Triolo et al. (2006 ). For a related structure, see: Pringle et al. (2003 ). For polymorphs of ionic liquids, see: Holbrey et al. (2003 ) and for the applications of ionic liquids, see: Plechkova & Seddon (2008 ).

Experimental

Crystal data

C₇H₁₂N₂O₃S
M_r = 204.25
Monoclinic, P 2₁ /c
a = 9.8164 (4) Å
b = 11.7421 (5) Å
c = 7.9769 (3) Å
β = 94.878 (2)°
V = 916.13 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 296 K
0.29 × 0.28 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: for a sphere (SADABS; Bruker, 2007 ) T_min = 0.910, T_max = 0.958
21327 measured reflections
8299 independent reflections
5726 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.120
S = 1.03
8299 reflections
166 parameters
All H-atom parameters refined
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O2ⁱ	0.923 (14)	2.197 (14)	2.9512 (9)	138.4 (12)
C5—H5A⋯O1ⁱⁱ	0.899 (14)	2.381 (15)	3.1573 (10)	144.6 (12)
C4—H4A⋯O1ⁱⁱⁱ	0.961 (14)	2.528 (14)	3.3268 (11)	140.5 (11)
C4—H4A⋯O3ⁱⁱⁱ	0.961 (14)	2.541 (14)	3.4364 (11)	155.0 (11)
C7—H7B⋯O3^iv	0.961 (12)	2.613 (12)	3.1693 (10)	117.2 (9)
C8—H8B⋯O3^iv	0.990 (14)	2.621 (13)	3.2086 (9)	118.1 (9)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x, -y+1, -z+1; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536810004344/kp2241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810004344/kp2241Isup2.hkl

checkCIF report

Comment top

Ionic liquids (ILs) have proven to be highly versatile materials with an ever expanding suite of chemical applications. An application that has recently shown great promise is the use of functionalized ILs as Brønsted acid catalysts for organic reactions (Cole et al., 2002). These IL catalysts are most commonly prepared by the reaction of 1-methylimidazolium-3-alkyl sulfonate zwitterion with an acid that has a pKa low enough to protonate the sulfonate group (Yoshizawa et al., 2001; Cole et al., 2002). The activity of the IL (e.g. the effectiveness of proton transfer) is significantly impacted by the structure and interactions of the zwitterion. It has been shown that the local structure of ILs is often conserved on transition from the solid state to the liquid state (Triolo et al., 2006; Henderson et al., 2007; Reichert et al., 2007). Thus, a structural analysis of the zwitterion, 1-methylimidaolium-3-propanesulfonate (I) might provide valuable insight into the activity of the Brønsted acid IL catalyst.

The asymmetric unit of the title compound is presented in Figure 1. The dominant intermolecular interactions are Coulombic in nature and are through the charged centers of the zwitterion: the imidazolium ring and the sulfonate group (Fig. 2). The negative charged sulfonate group is surrounded by four imidazolium head groups forming six close contacts (Table 1). The interactions of the imidazolium ring hydrogen atoms with the sulfonate group establish two three-dimensional R22(16) rings. The packing along the b axis (Fig. 3) shows the zwitterions arranged in columns along the c axis. The head-to-tail orientation maximizes the polar interaction and minimizes cation-cation and anion-anion repulsions.

Related literature top

For the use of functionalized ionic liquids (ILs) as Brønsted acid catalysts for organic reactions, see: Cole et al. (2002); Yoshizawa et al. (2001). The local structure of ILs is often conserved on transition from the solid state to the liquid state, see: Henderson et al. (2007); Reichert et al. (2007); Triolo et al. (2006). For a related structure, see: Pringle et al. (2003). For related literature on what subject?, see: Holbrey et al. (2003); Plechkova et al. (2008).

Experimental top

Compound I was synthesized following the procedure for similar zwitterionic compounds published by (Yoshizawa et al., 2001). 1,3-Propane sultone (25 g, 0.122 mol) was added dropwise to a solution of 1-methylimidazole (10 g, 0.122 mol) in acetone (40 ml) and stirred, then cooled on an ice bath overnight. A white precipitate was recovered from the reaction solution through filtration and washing with acetone. The product was then dried under vacuum giving a white solid (m.p. 482 K). A colourless crystal suitable for single crystal X-ray diffraction was retrieved from the dried product.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The thermal ellipsiod plot of the asymmetric unit of (I). The displacement ellipsiods are shown at the 50% probability level.
	Fig. 2. Close contacts in compound I.
	Fig. 3. Packing diagram along the b axis.
	Fig. 4. Reaction scheme.

3-(1-Methyl-3-imidazolio)propanesulfonate top

Crystal data top

C₇H₁₂N₂O₃S	F(000) = 432
M_r = 204.25	D_x = 1.481 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 482 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.8164 (4) Å	Cell parameters from 4851 reflections
b = 11.7421 (5) Å	θ = 3.1–41.1°
c = 7.9769 (3) Å	µ = 0.33 mm⁻¹
β = 94.878 (2)°	T = 296 K
V = 916.13 (6) Å³	Plate, colourless
Z = 4	0.29 × 0.28 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	8299 independent reflections
Radiation source: fine-focus sealed tube	5726 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
phi and ω scans	θ_max = 47.1°, θ_min = 3.1°
Absorption correction: for a sphere (SADABS; Bruker, 2007)	h = −20→13
T_min = 0.910, T_max = 0.958	k = −19→24
21327 measured reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	All H-atom parameters refined
S = 1.03	w = 1/[σ²(F_o²) + (0.0574P)² + 0.0483P] where P = (F_o² + 2F_c²)/3
8299 reflections	(Δ/σ)_max = 0.002
166 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₇H₁₂N₂O₃S	V = 916.13 (6) Å³
M_r = 204.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.8164 (4) Å	µ = 0.33 mm⁻¹
b = 11.7421 (5) Å	T = 296 K
c = 7.9769 (3) Å	0.29 × 0.28 × 0.13 mm
β = 94.878 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	8299 independent reflections
Absorption correction: for a sphere (SADABS; Bruker, 2007)	5726 reflections with I > 2σ(I)
T_min = 0.910, T_max = 0.958	R_int = 0.033
21327 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.120	All H-atom parameters refined
S = 1.03	Δρ_max = 0.55 e Å⁻³
8299 reflections	Δρ_min = −0.47 e Å⁻³
166 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1	0.288447 (16)	0.459431 (14)	0.711035 (19)	0.01929 (4)
O1	0.18103 (7)	0.54452 (5)	0.71911 (8)	0.02993 (12)
O2	0.42331 (6)	0.50523 (8)	0.76230 (9)	0.03616 (15)
O3	0.25705 (8)	0.35528 (5)	0.79823 (8)	0.03407 (14)
N3	0.17238 (6)	0.51000 (5)	0.16133 (7)	0.01989 (9)
N1	0.28516 (6)	0.65793 (5)	0.08981 (8)	0.02208 (9)
C2	0.29151 (7)	0.54584 (6)	0.11322 (8)	0.02096 (10)
H2A	0.3704 (14)	0.5037 (13)	0.1080 (19)	0.037 (3)*
C4	0.08588 (8)	0.60254 (6)	0.16753 (10)	0.02580 (12)
H4A	−0.0036 (14)	0.5991 (11)	0.2077 (16)	0.034 (3)*
C5	0.15675 (8)	0.69513 (7)	0.12222 (11)	0.02724 (13)
H5A	0.1323 (14)	0.7688 (12)	0.1137 (17)	0.037 (3)*
C6	0.39573 (9)	0.72763 (8)	0.03336 (12)	0.03149 (15)
H6A	0.3932 (15)	0.8024 (14)	0.0813 (19)	0.044 (4)*
H6B	0.4809 (19)	0.6923 (15)	0.063 (2)	0.061 (5)*
H6C	0.3820 (17)	0.7417 (17)	−0.081 (2)	0.067 (5)*
C7	0.14604 (8)	0.39419 (6)	0.21968 (8)	0.02303 (11)
H7A	0.0552 (13)	0.3717 (11)	0.1696 (15)	0.027 (3)*
H7B	0.2156 (12)	0.3490 (11)	0.1741 (15)	0.026 (3)*
C8	0.15267 (7)	0.38976 (6)	0.41105 (8)	0.02112 (10)
H8A	0.0853 (14)	0.4389 (12)	0.4510 (18)	0.033 (3)*
H8B	0.1301 (13)	0.3105 (12)	0.4405 (17)	0.036 (3)*
C9	0.29159 (7)	0.42456 (8)	0.49418 (9)	0.02574 (12)
H9A	0.3243 (16)	0.4859 (13)	0.444 (2)	0.043 (4)*
H9B	0.3600 (16)	0.3658 (13)	0.4885 (18)	0.043 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01791 (6)	0.02075 (7)	0.01894 (6)	−0.00086 (5)	0.00002 (4)	0.00099 (4)
O1	0.0309 (3)	0.0258 (2)	0.0325 (3)	0.0079 (2)	−0.0007 (2)	−0.00600 (19)
O2	0.0218 (2)	0.0569 (4)	0.0287 (3)	−0.0109 (3)	−0.0044 (2)	−0.0016 (3)
O3	0.0510 (4)	0.0231 (2)	0.0281 (2)	−0.0029 (2)	0.0032 (2)	0.00664 (19)
N3	0.0201 (2)	0.01929 (19)	0.02006 (19)	0.00022 (16)	0.00055 (16)	−0.00017 (15)
N1	0.0208 (2)	0.0222 (2)	0.0233 (2)	−0.00089 (18)	0.00185 (17)	0.00077 (17)
C2	0.0201 (2)	0.0225 (2)	0.0204 (2)	0.00164 (19)	0.00209 (18)	0.00037 (18)
C4	0.0200 (3)	0.0237 (3)	0.0339 (3)	0.0023 (2)	0.0034 (2)	0.0011 (2)
C5	0.0245 (3)	0.0214 (3)	0.0361 (3)	0.0030 (2)	0.0042 (2)	0.0014 (2)
C6	0.0295 (4)	0.0310 (3)	0.0347 (4)	−0.0069 (3)	0.0068 (3)	0.0048 (3)
C7	0.0289 (3)	0.0190 (2)	0.0207 (2)	−0.0029 (2)	−0.0008 (2)	−0.00147 (18)
C8	0.0208 (2)	0.0220 (2)	0.0204 (2)	−0.00162 (19)	0.00092 (18)	−0.00033 (18)
C9	0.0180 (2)	0.0392 (4)	0.0200 (2)	0.0002 (2)	0.00188 (18)	−0.0015 (2)

Geometric parameters (Å, º) top

S1—O3	1.4529 (6)	C5—H5A	0.899 (14)
S1—O2	1.4550 (6)	C6—H6A	0.959 (16)
S1—O1	1.4580 (6)	C6—H6B	0.945 (19)
S1—C9	1.7805 (7)	C6—H6C	0.924 (19)
N3—C2	1.3298 (9)	C7—C8	1.5233 (9)
N3—C4	1.3825 (9)	C7—H7A	0.982 (13)
N3—C7	1.4673 (9)	C7—H7B	0.961 (12)
N1—C2	1.3301 (9)	C8—C9	1.5207 (10)
N1—C5	1.3791 (10)	C8—H8A	0.952 (14)
N1—C6	1.4607 (10)	C8—H8B	0.990 (14)
C2—H2A	0.923 (14)	C9—H9A	0.898 (16)
C4—C5	1.3562 (11)	C9—H9B	0.967 (16)
C4—H4A	0.961 (14)

O3—S1—O2	113.68 (5)	H6A—C6—H6B	110.8 (14)
O3—S1—O1	111.84 (4)	N1—C6—H6C	110.7 (11)
O2—S1—O1	112.24 (5)	H6A—C6—H6C	102.9 (15)
O3—S1—C9	107.06 (4)	H6B—C6—H6C	112.0 (15)
O2—S1—C9	105.52 (4)	N3—C7—C8	110.85 (5)
O1—S1—C9	105.84 (4)	N3—C7—H7A	107.3 (7)
C2—N3—C4	108.62 (6)	C8—C7—H7A	111.0 (7)
C2—N3—C7	124.60 (6)	N3—C7—H7B	104.0 (7)
C4—N3—C7	126.28 (6)	C8—C7—H7B	112.9 (7)
C2—N1—C5	108.65 (6)	H7A—C7—H7B	110.4 (10)
C2—N1—C6	124.78 (7)	C9—C8—C7	112.84 (6)
C5—N1—C6	126.54 (7)	C9—C8—H8A	108.3 (8)
N3—C2—N1	108.77 (6)	C7—C8—H8A	110.0 (8)
N3—C2—H2A	127.3 (9)	C9—C8—H8B	111.1 (8)
N1—C2—H2A	123.6 (9)	C7—C8—H8B	106.2 (8)
C5—C4—N3	106.86 (7)	H8A—C8—H8B	108.4 (11)
C5—C4—H4A	128.8 (8)	C8—C9—S1	113.36 (5)
N3—C4—H4A	124.1 (8)	C8—C9—H9A	111.2 (10)
C4—C5—N1	107.09 (7)	S1—C9—H9A	106.8 (10)
C4—C5—H5A	130.7 (9)	C8—C9—H9B	112.9 (9)
N1—C5—H5A	122.2 (9)	S1—C9—H9B	106.2 (9)
N1—C6—H6A	110.2 (9)	H9A—C9—H9B	105.9 (13)
N1—C6—H6B	110.1 (11)

C2—N3—C7—C8	100.05 (8)	C4—N3—C7—C8	−70.97 (8)
N3—C7—C8—C9	−60.48 (8)	N3—C7—C8—C9	−60.48 (8)
C7—C8—C9—S1	163.00 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.923 (14)	2.197 (14)	2.9512 (9)	138.4 (12)
C5—H5A···O1ⁱⁱ	0.899 (14)	2.381 (15)	3.1573 (10)	144.6 (12)
C4—H4A···O1ⁱⁱⁱ	0.961 (14)	2.528 (14)	3.3268 (11)	140.5 (11)
C4—H4A···O3ⁱⁱⁱ	0.961 (14)	2.541 (14)	3.4364 (11)	155.0 (11)
C7—H7B···O3^iv	0.961 (12)	2.613 (12)	3.1693 (10)	117.2 (9)
C8—H8B···O3^iv	0.990 (14)	2.621 (13)	3.2086 (9)	118.1 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₇H₁₂N₂O₃S
M_r	204.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.8164 (4), 11.7421 (5), 7.9769 (3)
β (°)	94.878 (2)
V (Å³)	916.13 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.33
Crystal size (mm)	0.29 × 0.28 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	For a sphere (SADABS; Bruker, 2007)
T_min, T_max	0.910, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	21327, 8299, 5726
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	1.030

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.120, 1.03
No. of reflections	8299
No. of parameters	166
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.47

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	0.923 (14)	2.197 (14)	2.9512 (9)	138.4 (12)
C5—H5A···O1ⁱⁱ	0.899 (14)	2.381 (15)	3.1573 (10)	144.6 (12)
C4—H4A···O1ⁱⁱⁱ	0.961 (14)	2.528 (14)	3.3268 (11)	140.5 (11)
C4—H4A···O3ⁱⁱⁱ	0.961 (14)	2.541 (14)	3.4364 (11)	155.0 (11)
C7—H7B···O3^iv	0.961 (12)	2.613 (12)	3.1693 (10)	117.2 (9)
C8—H8B···O3^iv	0.990 (14)	2.621 (13)	3.2086 (9)	118.1 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) −x, −y+1, −z+1; (iv) x, −y+1/2, z−1/2.

Acknowledgements

Portions of this work were funded by the Office of Naval Research and the US Naval Academy Research Foundation. Any opinions, findings, and conclusion or recommendations expressed in this material are those of the author(s) and do not necessarily reflect the views of the US Navy.

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Volume 66| Part 3| March 2010| Page o591

doi:10.1107/S1600536810004344

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(1-Methyl-3-imidazolio)propane­sulfonate: a precursor to a Brønsted acid ionic liquid

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(1-Methyl-3-imidazolio)propanesulfonate: a precursor to a Brønsted acid ionic liquid