Abstract
Tetra-kis(2-methyl-prop-yl)thio-per-oxy-dicarbonic di-amide, or tetra-iso-butyl-thiuram di-sulfide, C18H36N2S4, crystallizes in a general position in the triclinic space group P-1 but shows pseudo-C2 symmetry about the di-sulfide bond. The C-S-S-C torsion angle [-85.81 (2)°] and the dihedral angle between the two NCS2 mean planes [85.91 (5)°] are within the range observed for this compound type. Multiple intra- and inter-molecular S⋯H-C close contacts appear to play a role in assisting the specific conformation of the pendant isobutyl groups and the packing arrangement of mol-ecules within the cell. Tetra-iso-butyl-thiuram di-sulfide mol-ecules of one optical configuration form sheets in the plane of the a and b axes. Inversion centers exist between adjoining sheets, which stack along the c axis and alternate in the handedness of their constituent mol-ecules.
Highlights
Inversion centers exist between adjoining sheets, which stack along the c axis and alternate in the handedness of their constituent molecules
Tetraethylthiuram disulfide, under the trade name disulfiram, is used for the treatment of chronic alcoholism because of its inhibitory effect upon liver alcohol dehydrogenase (Mutschler et al, 2016). It has received scrutiny for its ability to sensitize cancer cells to radiotherapy and to the effects of anticancer drugs (Jiao et al, 2016) as well as for its bactericidal action against drug-resistant Mycobacterium tuberculosis (Horita et al, 2012). Tetraalkylthiuram disulfides function both as chelating ligands themselves (Chieh, 1977; Chieh, 1978; Thirumaran et al, 2000; Saravanan et al, 2005; Prakasam et al, 2009) and as precursors to dithiocarbamate ligands, which are used in the coordination chemistry of both the transition metals (Hogarth, 2005) and main group elements (Heard, 2005)
Spectrum of N,N,N0,N0 - tetrakis(2-methylpropyl)thioperoxydicarbonic diamide itself does not show evidence of such intramolecular interaction, several recent studies of tetrathiuram disulfides have suggested such interactions in the crystalline state (Raya et al, 2005; Srinivasan et al, 2012; Nath et al, 2016). This possibility of similar weak interaction(s) in the crystal structure of tetraisobutylthiuram disulfide has motivated a determination of its structure by X-ray diffraction, reported
Summary
N,N,N0 ,N0 -Tetraalkylthioperoxydicarbonic diamides, commonly called tetrathiuram disulfides, comprise a class of organosulfur compounds with applications that are both diverse and long-standing. Tetraethylthiuram disulfide, under the trade name disulfiram, is used for the treatment of chronic alcoholism because of its inhibitory effect upon liver alcohol dehydrogenase (Mutschler et al, 2016) It has received scrutiny for its ability to sensitize cancer cells to radiotherapy and to the effects of anticancer drugs (Jiao et al., 2016) as well as for its bactericidal action against drug-resistant Mycobacterium tuberculosis (Horita et al, 2012). The room temperature 1H NMR spectrum of N,N,N0 ,N0 - tetrakis(2-methylpropyl)thioperoxydicarbonic diamide (tetraisobutylthiuram disulfide) itself does not show evidence of such intramolecular interaction, several recent studies of tetrathiuram disulfides have suggested such interactions in the crystalline state (Raya et al, 2005; Srinivasan et al, 2012; Nath et al, 2016) This possibility of similar weak interaction(s) in the crystal structure of tetraisobutylthiuram disulfide has motivated a determination of its structure by X-ray diffraction, reported . S H—C contacts and, importantly, that variable temperature 1H NMR spectroscopy be used to assess the importance of any such interactions in solution
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