2,3,5,6-Tetrakis(phenoxymethyl)pyrazine and 2,3,5,6-tetrakis(phenylsulfanylmethyl)pyrazine

Assoumatine, Tokouré; Gasser, Gilles; Stœckli-Evans, Helen

doi:10.1107/s010827010700710x

Cited by 4 publications

(4 citation statements)

References 7 publications

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“…In the phenyl analogue of the title compound, viz. 2,3,5,6-tetrakis[(phenylsulfanyl)methyl]pyrazine data reports (Assoumatine et al, 2007), the corresponding dihedral angles are 19.15 (7), 79.58 (7) and 60.45 (8) , respectively. In the crystal, molecules are linked via C-HÁ Á Á interactions, forming chains along [010]; see Table 1 and Fig.…”

Section: Structure Descriptionmentioning

confidence: 99%

“…The title compound is one of a series of tetra-substituted pyrazine compounds (Pacifico & Stoeckli-Evans, 2004;Assoumatine et al, 2007;Assoumatine & Stoeckli-Evans, 2014a), prepared in order to study their coordination behaviour with various transition metals (Assoumatine, 1999). It was synthesized by the reaction of 2,3,5,6-tetrakis(bromomethyl)pyrazine (Assoumatine & Stoeckli-Evans, 2014b), with 2-mercaptopyridine.…”

Section: Structure Descriptionmentioning

confidence: 99%

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2,3,5,6-Tetrakis{[(pyridin-2-yl)sulfanyl]methyl}pyrazine

Assoumatine

Stœckli-Evans

2016

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The title compound, C 28 H 24 N 6 S 4 , synthesized by the reaction of 2,3,5,6-tetrakis(bromomethyl)pyrazine with 2-mercaptopyridine, crystallizes with one half-molecule in the asymmetric unit. The whole molecule is generated by inversion symmetry, the centre of the pyrazine ring being located about an inversion centre. The pyridine rings of the unique (pyridin-2-ylsulfanyl)methyl substituents are inclined to the pyrazine ring by 38.7 (3) and 75.6 (2) , and by 66.0 (3) to one another. In the crystal, molecules are linked via C-HÁ Á Á interactions, forming chains along the b-axis direction. The chains are linked by offset -interactions [intercentroid distance = 3.682 (3) Å ], forming layers lying parallel to the bc plane. Structure descriptionThe title compound is one of a series of tetra-substituted pyrazine compounds (Pacifico & Stoeckli-Evans, 2004;Assoumatine et al., 2007;Assoumatine & Stoeckli-Evans, 2014a), prepared in order to study their coordination behaviour with various transition metals (Assoumatine, 1999). It was synthesized by the reaction of 2,3,5,6-tetrakis(bromomethyl)pyrazine (Assoumatine & Stoeckli-Evans, 2014b), with 2-mercaptopyridine. The synthesis and crystal structure of 2,3,5,6-tetrakis(bromomethyl)pyrazine have been reported (Assoumatine & Stoeckli-Evans, 2014b).The title compound, crystallizes with one half-molecule in the asymmetric unit (Fig. 1). The whole molecule is generated by inversion symmetry, the centre of the pyrazine ring being located about an inversion centre. The pyridine rings (N2/C4-C8 and N3/C10-C14) of the unique (pyridin-2-ylsulfanyl)methyl substituents are inclined to the pyrazine ring by 38.7 (3) and 75.6 (2) , respectively, and by 66.0 (3) to one another. In the phenyl analogue of the title compound, viz. 2,3,5,6-tetrakis[(phenylsulfanyl)methyl]pyrazine Keywords: crystal structure; tetrakis-substituted; pyrazine; pyridin-2-ylsulfanyl derivative; inversion symmetry; C-HÁ Á Á interactions; offsetinteractions. CCDC reference: 1521950Structural data: full structural data are available from iucrdata.iucr.org Synthesis and crystallizationTo a magnetically stirred solution of 2-mercaptopyridine (4 g, 35.4 mmol; Aldrich, 99%) in CH 2 Cl 2 (100 ml), were added 2,3,5,6-tetrakis(bromomethyl)pyrazine (4 g, 8.85 mmol) and triethylamine (5 ml, 35.4 mmol; Fluka, 99.5%). The contents were heated at reflux for 30 min, cooled to room temperature, and diluted with CH 2 Cl 2 (100 ml). The organic solution was washed with water (3 Â 30 ml) and a saturated solution of NaCl (1 Â 30 ml), dried over anhydrous MgSO 4 and evaporated to dryness on a rotary evaporator after filtration. The resultant yellowish residue was recrystallized from acetonitrile solution and dried under vacuum to afford the title compound (yield 4.56 g, 90%; m.p. 422-423 K). R f 0.48 (solvent CH 2 Cl 2 , eluent CHCl 3 /MeCO 2 Et, 7/5 v/v). Pale-yellow blocks were prepared by diffusion of an equal volume of ethanol into a concentrated CHCl 3 (4 ml) solution of the title compound. Spectroscopic and analytical data:...

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Section: Structure Descriptionmentioning

confidence: 99%

Section: Structure Descriptionmentioning

confidence: 99%

2,3,5,6-Tetrakis{[(pyridin-2-yl)sulfanyl]methyl}pyrazine

Assoumatine

Stœckli-Evans

2016

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“…For syntheses of the starting reagent, 2,3,5,6-tetrakis(bromomethyl)pyrazine, see: Ferigo et al (1994); Assoumatine (1999); Assoumatine & Stoeckli-Evans (2014). For the crystal structures of similar sulfanylmethyl derivatives of pyrazine, such as two triclinic polymorphs of 2,3,5,6 tetrakis(naphthalen-2-ylsulfanylmethyl)pyrazine both possessing inversion symmetry, see: Pacifico & Stoeckli-Evans (2004), and for 2,3,5,6-tetrakis(phenylsulfanylmethyl)pyrazine, which also crystallizes in space group P1 and possesses inversion symmetry, see: Assoumatine et al (2007 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al, 2008); software used to prepare material for publication: SHELXL2013, PLATON (Spek, 2009) and publCIF (Westrip, 2010…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure of 2,3,5,6-tetrakis[(methylsulfanyl)methyl]pyrazine

Assoumatine

Stœckli-Evans

2014

Acta Cryst E

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The title compound, C12H20N2S4, synthesized by the reaction of 2,3,5,6-tetrakis(bromomethyl)pyrazine with sodium methanethiolate, crystallizes with a half -molecule in the asymmetric unit. The whole molecule is generated by inversion symmetry; the inversion centre being located in the centre of the pyrazine ring. The molecule has an S-shaped conformation with two (methylsulfanyl)methyl substituent arms directed above the plane of the pyrazine ring and two below. The C(H3)—S—C(H2)—C(aromatic) torsion angles are 70.47 (18) and −67.65 (17)°, respectively. In the crystal, molecules are linked via weak C—H⋯S hydrogen bonds, forming chains along [001] and enclosing R 2 2(12) ring motifs. The chains are linked by further weak C—H⋯S hydrogen bonds, forming sheets lying parallel to (101).

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“…A small number of them involve 2,3,5,6tetrakis(aminomethyl)pyrazine (tampyz), which was used to prepare transition metal binuclear complexes, for example [Cl 2 Zn(tampyz)ZnCl 2 ], and a quasi-linear one-dimensional coordination polymer, {Mn(tampyz)Cl 2 Á2H 2 O} n (Ferigo et al, 1994). The title compound has also been used in the synthesis of two triclinic polymorphs of 2,3,5,6 tetrakis(naphthalen-2ylsulfanylmethyl)pyrazine (Pacifico & Stoeckli-Evans, 2004), 2,3,5,6-tetrakis((naphthalen-2-yloxy)methyl)pyrazine , 2,3,5,6-tetrakis(phenoxymethyl)pyrazine and 2,3,5,6-tetrakis(phenylsulfanylmethyl)pyrazine (Assoumatine et al, 2007). All five structures possess inversion symmetry.…”

Section: Figurementioning

confidence: 99%