Chemistry:Dithiobiuret
Dithiobiuret is an organosulfur compound with the formula HN(C(S)NH2)2. It is a colourless solid that is soluble in warm water and polar organic solvents. It is a planar molecule with short C-S and C-N distances (1.69, 1.38 Å, resp.) indicative of multiple C-S and C-N bonding.[1]
The compound can be viewed as the product from the condensation of two molecules of thiourea, but it is prepared by treatment of 2-cyanoguanidine with hydrogen sulfide. The conversion proceeds via guanylthiourea:
- NCNC(NH2) + H2S → HN(C(S)NH2)(C(NH)NH2)
- HN(C(S)NH2)(C(NH)NH2) + H2S → HN(C(S)NH2)2
It is used as a plasticizer, a rubber accelerator, and as an intermediate in pesticide manufacturing.[2]
Properties
Dithiobiuret binds to metals in a bidentate fashion, both as the neutral ligand and as its conjugate base.[3]
Safety
Dithiobiuret is extremely toxic; exposure can result in respiratory failure.
See also
References
- ↑ Spofford, W. A.; Amma, E. L. (1972). "Crystal and molecular structure of dithiobiuret". Journal of Crystal and Molecular Structure 2 (4): 151–158. doi:10.1007/BF01275491. Bibcode: 1972JCCry...2..151S.
- ↑ Dithiobiuret Hazardous Substance Fact Sheet, New Jersey Department of Health and Senior Services
- ↑ Pignedoli, A.; Peyronel, G.; Antolini, L. (1973). "The crystal and molecular structure of bis(2,4-dithiobiureto)nickel(II) diperchlorate–ethanol, Ni(HDTB)2(ClO4)2.EtOH". Acta Crystallographica Section B Structural Crystallography and Crystal Chemistry 29 (7): 1490–1499. doi:10.1107/S0567740873004796. Bibcode: 1973AcCrB..29.1490P.
External links
- Williams, KD; Porter, WR; Peterson, RE (1982). "Dithiobiuret metabolism in the rat". Neurotoxicology 3 (4): 221–31. PMID 6820683.
- Dithiobiuret at www.chemicalbook.com.
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