Structure of dibenzoyldisulphane, C14H10O2S2

Bis(N-methyl-N-phenylcarbamoyl)disulfane

“…The most noteworthy feature of the title compound is the torsion angle about the disulfane, which is 81.6° and as such is somewhat smaller than the theoretical optimum of 90.0° (Pauling, 1949;Torrico-Vallejos et al, 2010) that has been explained as allowing for minimal mutual repulsion of pπ orbital electron lone pairs in sulfur. A comparable deviation from theory was reported for dibenzoyl disulfide (Rout et al, 1983;Paul & Srikrishnan, 2004), where the torsion angle is 80.8°. Bis(Nmethyl-N-phenylthiocarbamoyl)disulfane, which only differs from the title compound by two thiocarbonyls in place of two carbonyls, has a torsion angle about the disulfane of 89.8° and shows a conformation that is not completely superimposable on the title compound (Fun et al, 2001).…”

“…Several other reference compounds also have an S-S bond length of 2.01-2.03 Å (Bereman et al, 1983;Rout et al, 1983;Paul and Srikrishnan, 2004;Fun et al, 2001;Raya et al, 2005;Li et al, 2006;Singh et al, 2011). The most noteworthy feature of the title compound is the torsion angle about the disulfane, which is 81.6° and as such is somewhat smaller than the theoretical optimum of 90.0° (Pauling, 1949;Torrico-Vallejos et al, 2010) that has been explained as allowing for minimal mutual repulsion of pπ orbital electron lone pairs in sulfur.…”

“…For the preparation of the title compound, and of very closely related chemical structures, see: Kobayashi et al (1973); Barany et al (1983); Schroll & Barany (1986); Schrader et al (2011). For related structures, see: CSD refcodes BOWGAV (Bereman et al, 1983), DBZOSS01&03 (Rout et al, 1983;Paul & Srikrishnan, 2004), METHUS03 (Wang & Liao, 1989), NELTUT (Fun et al, 2001), JAXPOO (Raya et al, 2005), UDALER (Li et al, 2006) and EMASIV (Singh et al, 2011). For the theoretical optimum torsion angle about the disulfane, see: Pauling (1949) Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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.…”

Bis[(methylsulfanyl)carbonyl]disulfane

“…For the preparation of the title compound and for the preparation and structures of the corresponding trisulfane and tetrasulfane compounds, see: Mott & Barany (1984). For other related structures, see: Bereman et al (1983); Rout et al (1983); Paul & Srikrishnan (2004); Li et al (2006); Schroll et al (2012). For a description of the Cambridge Structural Database, see: Allen (2002).…”

“…This phenomenon is quite general and has been observed for related compounds. In all, a search of the Cambridge Database for compounds of the formula R(C═O)SS(C═O)R provided four different compounds for comparison [CSD refcodes: BOWGAV (Bereman et al, 1983), DBZOSS01&03 (Rout et al, 1983;Paul & Srikrishnan, 2004), UDALER (Li et al, 2006), and 880326 (Schroll et al, 2012)]. The most noteworthy feature of our newly reported structure is that the torsion angle about the disulfane was 90.99°, which comes closer to the theoretical optimum of 90° (Pauling, 1960) than any other of the comparison compounds with the exception of bis(N,N-dicyclohexylsulfanylcarbamoyl)disulfane, where this angle is 89.7° (Li et al, 2006).…”