Bis(N-methyl-N-phenylcarbamoyl)disulfane

Abstract

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)°].

Crystal structures of (N-methyl-N-phenylamino)(N-methyl-N-phenylcarbamoyl)sulfide and the corresponding disulfane

“…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, S 8 (2.07 Å ), but slightly longer than the 2.03 Å found for bis (N-methyl-N-phenylcarbamoyl) (Schroll et al, 2012). In compound (III) (Fig.…”

“…A search for similar structures in the Cambridge Structural Database (CSD; Version 5.36, update of November 2014; Groom & Allen, 2014) gave bis(N-methyl-N-phenylcarbamoyl)disulfane (III), published previously from our research (Schroll et al, 2012), as well as two similar bis(carbamoyl)disulfanes (Bereman et al, 1983;Li et al, 2006 The molecular conformation of compound (I), showing 50% probability displacement ellipsoids with all non-H atoms labeled and numbered.…”