Tetra­ethyl­ammonium toluene-4-sulfon­ate

Diana Malgorzata Brus; Justyna Czyrko; Krzysztof Brzezinski

doi:10.1107/S1600536813002961

. 2013 Feb 2;69(Pt 3):o324. doi: 10.1107/S1600536813002961

Tetraethylammonium toluene-4-sulfonate

Diana Malgorzata Brus ^a, Justyna Czyrko ^a, Krzysztof Brzezinski ^a,^*

PMCID: PMC3588542 PMID: 23476522

Abstract

There are two tetraethylammonium cations and two toluene-4-sulfate anions in the asymmetric unit of the title salt, C₈H₂₀N⁺·C₇H₇O₃S⁻. One of the anions is disordered over two positions, with refined occupancies of 0.447 (3) and 0.553 (3). In the crystal, the cations and anions are linked by C—H⋯O hydrogen bonds, forming ribbons along [10-1]. The ribbons are linked via C—H⋯O hydrogen bonds, forming a two-dimensional network lying parallel to (10-1).

Related literature

For the preparation of tetraethylammonium toluene-4-sulfonate from ethyl 4-toluenesulfonate and triethylamine, see: Baizer (1964 ▶). For its application as a phase-transfer catalyst, see: Cerveau et al. (2002 ▶) or as the supporting electrolyte, see: Adachi et al. (1979 ▶); Wynne & Street (1985 ▶); Yoshida et al. (1986 ▶); Wong & Moeller (1993 ▶); Ben et al. (2011 ▶).

Experimental

Crystal data

C₈H₂₀N⁺·C₇H₇O₃S⁻
M _r = 301.21
Monoclinic,
a = 16.8771 (3) Å
b = 7.53713 (16) Å
c = 26.2404 (6) Å
β = 97.2938 (18)°
V = 3310.90 (12) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 100 K
0.8 × 0.6 × 0.3 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.771, T _max = 1.000
6276 measured reflections
6276 independent reflections
5477 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.076
wR(F ²) = 0.163
S = 1.19
6276 reflections
406 parameters
82 restraints
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXD (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Click here for additional data file.^{(40.7KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813002961/kp2445sup1.cif

e-69-0o324-sup1.cif^{(40.7KB, cif)}

Click here for additional data file.^{(307.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813002961/kp2445Isup2.hkl

e-69-0o324-Isup2.hkl^{(307.2KB, hkl)}

Click here for additional data file.^{(6.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813002961/kp2445Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6B—H6B⋯O23	0.95	2.57	3.351 (6)	140
C31—H31B⋯O3B ⁱ	0.99	2.49	3.344 (4)	145
C33—H33A⋯O2B	0.99	2.47	3.354 (4)	148
C35—H35A⋯O22ⁱⁱ	0.99	2.42	3.228 (4)	138
C36—H36C⋯O3B ⁱⁱⁱ	0.98	2.58	3.544 (4)	169
C43—H43B⋯O22	0.99	2.44	3.269 (4)	141
C45—H45A⋯O2B	0.99	2.53	3.367 (4)	142
C47—H47A⋯O3B ⁱ	0.99	2.57	3.440 (4)	147
C48—H48B⋯O22^iv	0.98	2.58	3.562 (4)	175

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The X-ray diffractometer was funded by the EFRD as part of the Operational Programme Development of Eastern Poland 2007–2013, project POPW.01.03.00–20-034/09–00.

supplementary crystallographic information

Comment

Tetraethylammonium toluene-4-sulfonate is applied as the phase-transfer catalyst in the preparation of bis-silanetriols (Cerveau et al., 2002). The compound is also widely used in electrochemistry as the supporting electrolyte (Wynne et al., 1985; Yoshida et al., 1986; Wong et al., 1993; Ben et al., 2011), because it could be easly removed from the reaction by the extraction with water (Adachi et al., 1979).

The asymmetric unit contains two tetraethylammonium cations and two toluene-4-sulfate anions (Fig. 1). One of the toluene-4-sulfate ions is disordered and is modeled in the two locations. The occupancy of two major positions in the final model is refined to 0.447 (3) and 0.553 (3). Within the crystal lattice the columns of cations and anions are formed along b and ac directions (Figs. 2 and 3, respectively).

Experimental

The title compound was prepared according to the procedure described by Baizer (1964). Briefly, ethyl toluene-4-sulfonate (200 g, 1.0 mole) was dissolved in 100 mL of anhydrous ethanol and triethylamine was added (101 g, 1.0 mole). The reaction mixture was stirred and heated under reflux for 6 h. The excess of triethylamine and ethanol was removed in vacuo. The crude product was washed several times with a dry ethylether and recrystallized from ethanol.