Thiuram monosulfides

structure of tetramethylthiuram monosulfide. The C=S and C-S distances are 166, 179 picometers. Color code: yellow = S, blue = N.[1]

Thiuram monosulfides are a class of organosulfur compounds with the formula (R2NCS)2S (R = organic group). Many examples are known, but popular ones include R = Me and R = Et. They are typically yellow solids that are soluble in polar organic solvents.[2]

Structure, synthesis

Thiuram monosulfides feature a pair planar thioamide subunits linked by a sulfur atom.[1]

Thiuram monosulfides can be prepared by desulfurization of thiuram disulfides[2] Treatment of a thiuram disulfide with triphenylphosphine, or with cyanide salts, yields the corresponding thiuram sulfide:

(R2NC(S)S)2 + PPh3 → (R2NCS)2S + S=PPh3 (Ph = C6H5)

References

  1. 1 2 Colapietro, M.; Domenicano, A.; Vaciago, A. (1976). "The crystal and molecular structure of tetramethylthiuram monosulphide". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry. 32 (9): 2581–2587. Bibcode:1976AcCrB..32.2581C. doi:10.1107/S0567740876008303.
  2. 1 2 Schubart, Rüdiger (2026). "Dithiocarbamic Acid and Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–28. doi:10.1002/14356007.a09_001.pub2. ISBN 978-3-527-30385-4.
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