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Crystal structures of (N-methyl-N-phenyl-amino)(N-methyl-N-phenyl-carbamoyl)sulfide and the corresponding disulfane.

Henley MJ, Schroll AL, Young VG, Barany G - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The title compounds, (N-methyl-N-phenyl-amino)(N-methyl-N-phenyl-car-bam-oyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenyl-amino)-(N-methyl-N-phenyl-carbamo-yl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chloro-carbon-yl)sulfenyl chloride and (chloro-carbon-yl)disulfanyl chloride, respectively.The torsion angle about the S-S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°.In the crystal of (II), non-classical inter-molecular C-H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R 2 (2)(10)], while inter-dimer C-H⋯S inter-actions generate chains extending along the b axis.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

ABSTRACT
The title compounds, (N-methyl-N-phenyl-amino)(N-methyl-N-phenyl-car-bam-oyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenyl-amino)-(N-methyl-N-phenyl-carbamo-yl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chloro-carbon-yl)sulfenyl chloride and (chloro-carbon-yl)disulfanyl chloride, respectively. The torsion angle about the S-S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical inter-molecular C-H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R 2 (2)(10)], while inter-dimer C-H⋯S inter-actions generate chains extending along the b axis.

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Structures of selected comparison compounds, bis­(N-methyl-N-phenyl­carbamo­yl)disulfane, (III), and bis­(N-methyl-N-phenyl­amino)­tris­ulfane, (IV)
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fig3: Structures of selected comparison compounds, bis­(N-methyl-N-phenyl­carbamo­yl)disulfane, (III), and bis­(N-methyl-N-phenyl­amino)­tris­ulfane, (IV)

Mentions: The title compounds differ by the number of sulfur atoms: one in (I) (Fig. 1 ▸) versus two in (II) (Fig. 2 ▸), and by the resulting relative orientations of the Ph(Me)N(C=O)S and N(Me)Ph moieties. Otherwise, they share similar bond lengths and angles across all analogous bonds (Table 1 ▸). Furthermore, the mol­ecular parameters are all within expected ranges. The S—S bond of (II) is 2.0625 (5) Å, which is comparable to the bond length in elemental sulfur, S8 (2.07 Å), but slightly longer than the 2.03 Å found for bis­(N-methyl-N-phenyl­carbamo­yl)di­sul­fane ([Ph(Me)N(C=O)S]2) (III) (Schroll et al., 2012 ▸). In compound (III) (Fig. 3 ▸), the slight shortening of the S—S bond was attributed to a partial double-bond character imparted by the adjacent carbonyl groups. Because (II) is essentially (III) minus one carbonyl group, it is not surprising for the S—S bond length in (II) to be closer to that in S8. The torsion angle about the S—S bond in (II) is −92.62 (6)°, which is comparable to the theoretical optimum of 90° (Pauling, 1949 ▸; Torrico-Vallejos et al., 2010 ▸).


Crystal structures of (N-methyl-N-phenyl-amino)(N-methyl-N-phenyl-carbamoyl)sulfide and the corresponding disulfane.

Henley MJ, Schroll AL, Young VG, Barany G - Acta Crystallogr E Crystallogr Commun (2015)

Structures of selected comparison compounds, bis­(N-methyl-N-phenyl­carbamo­yl)disulfane, (III), and bis­(N-methyl-N-phenyl­amino)­tris­ulfane, (IV)
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645008&req=5

fig3: Structures of selected comparison compounds, bis­(N-methyl-N-phenyl­carbamo­yl)disulfane, (III), and bis­(N-methyl-N-phenyl­amino)­tris­ulfane, (IV)
Mentions: The title compounds differ by the number of sulfur atoms: one in (I) (Fig. 1 ▸) versus two in (II) (Fig. 2 ▸), and by the resulting relative orientations of the Ph(Me)N(C=O)S and N(Me)Ph moieties. Otherwise, they share similar bond lengths and angles across all analogous bonds (Table 1 ▸). Furthermore, the mol­ecular parameters are all within expected ranges. The S—S bond of (II) is 2.0625 (5) Å, which is comparable to the bond length in elemental sulfur, S8 (2.07 Å), but slightly longer than the 2.03 Å found for bis­(N-methyl-N-phenyl­carbamo­yl)di­sul­fane ([Ph(Me)N(C=O)S]2) (III) (Schroll et al., 2012 ▸). In compound (III) (Fig. 3 ▸), the slight shortening of the S—S bond was attributed to a partial double-bond character imparted by the adjacent carbonyl groups. Because (II) is essentially (III) minus one carbonyl group, it is not surprising for the S—S bond length in (II) to be closer to that in S8. The torsion angle about the S—S bond in (II) is −92.62 (6)°, which is comparable to the theoretical optimum of 90° (Pauling, 1949 ▸; Torrico-Vallejos et al., 2010 ▸).

Bottom Line: The title compounds, (N-methyl-N-phenyl-amino)(N-methyl-N-phenyl-car-bam-oyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenyl-amino)-(N-methyl-N-phenyl-carbamo-yl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chloro-carbon-yl)sulfenyl chloride and (chloro-carbon-yl)disulfanyl chloride, respectively.The torsion angle about the S-S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°.In the crystal of (II), non-classical inter-molecular C-H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R 2 (2)(10)], while inter-dimer C-H⋯S inter-actions generate chains extending along the b axis.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455, USA.

ABSTRACT
The title compounds, (N-methyl-N-phenyl-amino)(N-methyl-N-phenyl-car-bam-oyl)sulfide, C15H16N2OS, (I), and (N-methyl-N-phenyl-amino)-(N-methyl-N-phenyl-carbamo-yl)disulfane, C15H16N2OS2, (II), are stable derivatives of (chloro-carbon-yl)sulfenyl chloride and (chloro-carbon-yl)disulfanyl chloride, respectively. The torsion angle about the S-S bond in (II) is -92.62 (6)°, which is close to the theoretical value of 90°. In the crystal of (II), non-classical inter-molecular C-H⋯O hydrogen bonds form centrosymmetric cyclic dimers [graph set R 2 (2)(10)], while inter-dimer C-H⋯S inter-actions generate chains extending along the b axis.

No MeSH data available.


Related in: MedlinePlus