Bis(N,N-dicyclohexylthiocarbamoyl) disulfide

Abstract

Key indicatorsSingle-crystal X-ray study T = 298 K Mean (C-C) = 0.004 Å R factor = 0.047 wR factor = 0.127 Data-to-parameter ratio = 16.1 For details of how these key indicators were automatically derived from the article, see

Bis(N,N-dibenzylthiocarbamoyl) disulfide

“…In (I) ( Fig. 1), the S-S bond length of 1.9910 (13) Å is slightly shorter than that observed in bis(N,N-dicyclohexylthiocarbamoyl) disulfide (Li et al, 2006) and in free (uncoordinated) disulfides (Kumar et al, 1990). The torsion angle C1-S1-S3-C16 is À85.71 (13) .…”

“…In a continuation of our study of thiocarbamate derivatives containing disulfide fragments (Li et al, 2006), we present here the title compound, (I) (also called tetrabenzylthiuram disulfide), prepared by oxidation of N,N-dibenzylthiocarbamic acid with iodine.…”

Bis(N-methyl-N-phenylcarbamoyl)disulfane

“…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.…”

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

“…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.…”