Structure of 5-(p-methoxyphenyl)-3H-1,2-dithiole-3-thione, C10H8OS3

Wang, Y.; Lin, Henry C.; Wei, Chin Hsuan

doi:10.1107/s0108270185007284

Cited by 4 publications

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“…In our previous studies, it was shown that the pyrazine ring is linked to 4-methyl-3H-1,2-dithiole-3-thione via a C-C bond to yield oltipraz (Wei, 1983), or to 4-methyl-3H-1,2-dithiol-3-one to form an oltipraz analog (Wei, 1985a). On the other hand, the 3H-1,2-dithiole-3-thione ring could be linked to a p-methoxyphenyl group, yielding 5-(pmethoxyphenyl)-3H-1,2-dithiole-3-thione (Wang, Lin & Wei, 1985). The present paper reports the structures in which a phenyl ring replaces an H atom of the 3H-1,2-dithiole-3-thione ring at two different positions.…”

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“…The author is particularly indebted to Dr C. R. Richmond, Associate Director of ORNL, for the arrangement of financial support. 3H-1,2-dithiole-3-thione or 3H-1,2-dithiol-3-one Angle between plane normals for six-and S-S C-S C-C five-membered (thione) (central) rings 4-Methyl-3H-1,2-di-2.047 A 1.627 A -thiole-3-thione* 4-Methyl-5-(2-pyra-2.049 (1) 1.655 (2) 1.480 (3) A 3.71 (8) ° zinyl)-3H-1,2-dithiole-2.041 (1) 1.670 (2) 1.480 (3) 8.92 (9) 3-thione~" 5-(p-Methoxyphenyl)-2.047 (1) 1.666 (3) 1.461 (3) 7.7 (1) 3H-1,2-dithiole-3-thione¢ 4-Methyl-5-(2-pyraz-2.035 (1) Wei (1985). § Wei (1985a).…”

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Structures of two isomers of phenyl-3H-1,2-dithiole-3-thione

Wei¹

1986

Acta Crystallogr C

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Abstract. Structures of two isomeric compounds are reported: 4-phenyl-3H-1,2-dithiole-3-thione (4-PDT) and 5-phenyl-3H-1,2-dithiole-3-thione (5-PDT). Both have formula C6Hs.C3HS3, M r = 210.339, X-ray data collected with 2(Mo K~tl) = 0.7093 A at 296 (1) K. The former belongs to the monoclinic space group P2Jc, a = 17.827 (4), b = 5.731 (1), c= 9.272 (2)A, fl= 91.93(2) ° , V=946.8(3)A 3, Z=4, Dm=l.47(1), D x=l.475gcm -3, g=6-93cm -~, F(000)=432. Final R(F)=0.031 for 2255 counter data with Fo2___ 2a(Fo2). The latter crystallizes in the orthorhombic space group Pbca, a= 19.949 (6), b= 12.188 (3), c = 7.544 (2) A, V= 1834.2 (9) A 3, Z = 8, D m = 1.51 (1), D x = 1.523 gcm -3, g = 7.16 cm -1, F(000) = 864. Final R(F)= 0.031 for 1633 data with Fo 2 > 20(Fo2). The molecules are composed of a phenyl ring and a five-membered heterocyclic ring, the difference between the two isomers being the positions of the C atom of the 3H-1,2-dithiole-3-thione ring to which the phenyl ring is linked. The two molecules have bond lengths and angles resembling each other and other compounds containing 3H-1,2-ditb.iole-3-thione as a building unit. The phenyl rings and the fivemembered-ring systems are both planar to within 0.01 A in both structures, the angle between the two plane normals being 67.40(9) ° for 4-PDT and 29.36 (8) ° for 5-PDT.

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Structures of two isomers of phenyl-3H-1,2-dithiole-3-thione

Wei¹

1986

Acta Crystallogr C

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“…(1:1) Complex 1,4,7,10,13,16,19-heptaoxacycloeicosane and ;>-methoxybenzenediazonium tetrafluoroborate: Groth (1981); (A) l-(4-methoxybenzylidene)-pyrazolidone-(3)-betaine: Kulpe et al (1982); (i) 2-(N-4-methoxyphenylaminomethylene)-1,3-indanedione: Aldoshin et al (1984); (j) 5-(p-methoxyphenyl)-3//-1.2-dithiole-3thione: Wang et al (1985); (/c) l,2-bis(p-methoxyphenylsulfonyl)ethane: Hauback et al (1988); (/) MSOzpmoPS: this work.…”

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confidence: 99%

Crystal structure of 1-(methylsulfonyl)- 2-(p-methoxyphenylthio)ethane at 87 K. A comparative study of two different crystals

Hauback¹,

Mo²

1990

Zeitschrift Für Kristallographie - Crystalline Materials

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The structure of l-(methylsulfonyl)-2-(p-methoxyphenylthio)ethane, C10H14O3S2, was determined from an X-ray diffraction study of two different crystals, A and B, at 87 K. The space group is monoclinic, Pljc, a = 10.859(1), b = 5.310(1), c = 19.934 (3) 98.49(2)° and Z = 4 from high-order reflections for crystal B. Intensities were collected to (sin 0)ß = 0.650 for crystal A and to 0.904 Ä"' for B with MoÄa radiation. The structure was solved by direct methods. Parameters derived for crystal A (Ä = 0.029 for 2418 FJ and from the data with (sin0)/ X < 0.650 Ä"' for B (Ä = 0.032 for 2402 F,) were compared and analysed by half-normal probability plots and by x^ tests. The agreement is very good. The slopes in all plots are < 1.0 indicating a slight overestimation of the Standard deviates. A normal probability plot of the two sets of observed F^ [(sin 9)/X < 0.65 Ä~'] has a siope very dose to 1.0. Least-squares refmements have been carried out with various subsets of data for crystal B. The Parameters from the refmement with (sin 0)/A > 0.75 Ä"' were taken to give the best description of the structure (/? = 0.027, 1387 F"). The refined bond lengths in the fragment containing S and the phenyl ring were corrected for thermal motion. Before correction the ring C -C bonds are about 0.0034 Ä longer than the values from the refinement with all data. Bonding Parameters at the S atoms corroborate previous observations for some closely related sulfide and sulfone structures. The distortions from €2« symmetry in the para-substituted phenyl ring is largely effected by the OCH 3 group which is confirmed from a comparison of various parasubstituted anisoles. The observed reversible change in colour of the crystals, from colourless at room temperature to pale purple at 87 K seems to be related to a shortening of an intermolecular S • • • Ph contact.

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“…X-Ray methods for 1,3-dithiolanes have shown the SÀS bond distances to be in the range of acyclic disulfides [91]. Figure 11.1 shows the bond lengths and angles of 1,2-dithiol-3-thione [93]. The 1 H NMR spectrum of 1,2-dithiolane 84 has signals at d2.09 ppm for H4 and d3.36 ppm for H3 and H5 [91].…”

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Five‐Membered Heterocycles with Two Heteroatoms: O and S Derivatives

Wilkins¹

2011

Modern Heterocyclic Chemistry

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Structure of 5-(p-methoxyphenyl)-3H-1,2-dithiole-3-thione, C10H8OS3

Cited by 4 publications

References 6 publications

Structures of two isomers of phenyl-3H-1,2-dithiole-3-thione

Structures of two isomers of phenyl-3H-1,2-dithiole-3-thione

Crystal structure of 1-(methylsulfonyl)- 2-(p-methoxyphenylthio)ethane at 87 K. A comparative study of two different crystals

Five‐Membered Heterocycles with Two Heteroatoms: O and S Derivatives

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