2-[(Dodecylsulfanyl)carbonothioyl­sulfanyl]­propanoic acid

Shude Xiao; Paul A Charpentier

doi:10.1107/S1600536811007963

. 2011 Mar 9;67(Pt 4):o811. doi: 10.1107/S1600536811007963

2-[(Dodecylsulfanyl)carbonothioylsulfanyl]propanoic acid

Shude Xiao ^a, Paul A Charpentier ^a,^*

PMCID: PMC3099875 PMID: 21754097

Abstract

In the title compound, C₁₆H₃₀O₂S₃, the decyl chain adopts an extended zigzag conformation. Two molecules are disposed about a center of inversion, forming an O—H⋯O hydrogen-bonded dimer.

Related literature

For use in polymerization of acrylic acid and acrylates, see: Alb et al. (2008 ▶, 2009 ▶); Konkolewicz et al. (2009 ▶). Various vinyl monomers can be polymerized via the RAFT (addition-fragmentation chain-transfer) mechanism by varying the substitutes of the trithiocarbonates, see: Moad et al. (2005 ▶, 2008 ▶). For related structures, see: Xiao & Charpentier (2010 ▶, 2011 ▶).

Experimental

Crystal data

C₁₆H₃₀O₂S₃
M _r = 350.58
Triclinic,
a = 6.5632 (4) Å
b = 7.0872 (4) Å
c = 22.0276 (14) Å
α = 85.819 (2)°
β = 86.873 (2)°
γ = 68.313 (2)°
V = 949.13 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 150 K
0.14 × 0.08 × 0.06 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.949, T _max = 0.977
40281 measured reflections
4522 independent reflections
3696 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.098
S = 1.08
4522 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007963/ng5117sup1.cif

e-67-0o811-sup1.cif^{(18.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007963/ng5117Isup2.hkl

e-67-0o811-Isup2.hkl^{(221.5KB, hkl)}

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
O1—H1⋯O2ⁱ	0.84	1.79	2.6292 (15)	175

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Canadian Natural Sciences and Engineering Research Council (NSERC) Idea to Innovation (I2I) Program. The authors are grateful to Dr Guerman Popov in the Department of Chemistry, the University of Western Ontario, for the data acquisition and interpretation.

supplementary crystallographic information

Comment

Trithiocarbonates are a type of chain transfer agents (CTA) that are used in addition-fragmentation chain-transfer (RAFT) polymerization. Various vinyl monomers can be polymerized via the RAFT mechanism by varying the substitutes of the trithiocarbonates (Moad et al., 2005, 2008). 2-(Dodecylthiocarbonothioylthio)propanoic acid was synthesized as the RAFT-CTA mainly for polymerization of acrylic acid and acrylates, but a few other vinyl monomers were also successfully polymerized, such as acrylonitrile / 1,3-butadiene and N-isopropylacrylamide. From solution or emulsion RAFT polymerization, diblock and triblock copolymers were prepared from acrylates/acrylic acid and other vinyl monomers. Via its carboxylic acid group, 2-(dodecylthiocarbonothioylthio)propanoic acid was immobilized onto nanoparticles, such as SiO₂ and carbon black, followed by RAFT polymerization yielding hybrid nanocomposites.

Experimental

1-Dodecanethiol 20 g (0.1 mol), triethylamine 12 g (0.12 mol) were mixed in THF 30 ml, and then carbon disulfide 11 g was added into the mixture dropwise at room temperature. The mixture was kept stirred for 1 day, and 2- bromopropionic acid 15.3 g (0.1 mol) / THF 5 ml were charged into it. The reaction lasted for 2 days at room temperature. Excess ethyl ether was used to precipitate the salts, and the solvents were evaporated. The crude product was treated with hydrobromic acid followed by extraction with ethyl ether. When the solvents were being removed, toluene was added to get rid of the residual water. Yellow crystals of 2-(dodecylthiocarbonothioylthio)propanoic acid were obtained from recrystalization in hexane/cyclohexane (10:1). m.p.: 77.21°C (DSC).