Ethane-1,2-diyl bis(benzenedithioate)

Abstract

In the crystal structure, the title compound, C16H14S4, is located on an inversion center and exhibits a gauche+–trans–gauche− conformation in the S—CH2—CH2—S bond sequence. The S—C=S plane makes a dihedral angle of 30.63 (17)° with the phenyl ring. An inter­molecular C—H⋯π inter­action is observed.

Butane-1,4-diyl bis(benzenecarbodithioate)

“…In general, the S-CH 2 single bond prefers the gauche state (Sawanobori et al, 2001;Sasanuma et al, 2002). For instance, the crystalline 2DBS 4 molecule adopts the g + tgconformation in the S-CH 2 -CH 2 -S linkage (Abe et al, 2011). By contraries, the two S-CH 2 bonds of 4DBS 4 were found here to be in the trans conformation.…”

“…For crystal structures and conformations of C 6 H 5 C( S)S-(CH 2 ) 2 SC( S)C 6 H 5 and C 6 H 5 C( O)S(CH 2 ) 4 SC( O)C 6 H 5 , see: Abe et al (2011Abe et al ( , 2013. For related compounds, see: Sawanobori et al (2001); Sasanuma et al (2002).…”

Chemistry of aromatic polythioesters and polydithioesters

“…These models also show gauche and trans preferences in the S-CH 2 and CH 2 -CH 2 bonds, respectively, being most stabilized in the g + tg − (termed often 'kink') conformation, which renders the two phenyl rings parallel and forms an intramolecular dipole-dipole attraction. 25,26 Because the difference in electronegativity between carbon and oxygen is larger than that between carbon and sulfur, the -S-CvO group is superior to -S-CvS in dipole moment. Accordingly, the g + tg − conformer of 2DBS 2 has a ΔG k value of −3.13 kcal mol −1 , while that of 2DBS 4 was evaluated to be −2.08 kcal mol −1 .…”

Molecular design, synthesis and characterization of aromatic polythioester and polydithioester

“…Commercially available chemicals were used as received: benzoyl-carbonyl- 13 C chloride (Isotec, 99 atom % 13 C); benzoyl chloride (Kanto Chemical); benzene-d 6 and silica gel (Merck); cyclohexane, 1,2-ethanedithiol, and Lawesson's reagent (Sigma-Aldrich); a,a 0 -dichloro-p-xylene, hexafluoroisopropanol, and terephthaloyl dichloride (Tokyo Chemical Industry); acetone, anhydrous magnesium sulfate, anhydrous sodium sulfate, calcium chloride, chloroform, chloroform-d, cyclohexanone, dichloromethane, 1,2-dibromoethane, diethyl ether, N,N-dimethylformamide, dimethyl sulfoxide, dimethyl-d 6 sulfoxide, ethanol, n-hexane, hydrochloric acid, iodomethane, methanol, odichlorobenzene, phenol, piperidine, sodium bicarbonate, sodium methoxide, sulfuric acid, triethylamine, trifluoroacetic acid, and xylene (Wako Pure Chemical Industries). Pyridine and toluene (Wako) were distilled before use.…”

“…1). For these models, the following experiments and computations were conducted: 1 H and 13 C NMR; singlecrystal X-ray diffraction; molecular orbital (MO) calculations. With conformational free energies and geometrical parameters derived from the models, the refined rotational isomeric state (RIS) scheme 12 was applied to PETS 2 and PETS 4 to predict their configurational properties and thermodynamic parameters.…”