Research Article: Bis(N-methyl-N-phenyl­carbamo­yl)disulfane

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): Alayne L. Schroll, Maren Pink, George Barany.


The title compound, C16H16N2O2S2, has been synthesized by several different high-yield routes, and has been encountered as a co-product in a number of reaction pathways, ever since it became of inter­est to our research program over 30 years ago. We now confirm the proposed mol­ecular structure in which the mol­ecule exhibits a twofold axis of symmetry through the mid-point of the S—S bond and the two planes defined by the (carbamo­yl)sulfenyl moieties are essentially perpendicular to each other [dihedral angle = 81.55 (14)°].

Partial Text

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 ▶); Torrico-Vallejos et al. (2010 ▶) and references cited therein.