Dithiocarbamate

 ( Cyp3a4 Inhibitors ) 

In organic chemistry, a dithiocarbamate is a chemical compound with the general formula . It contains the functional group with the structure . It is the analog of a carbamate in which both oxygen atoms are replaced by sulfur atoms (when only one oxygen is replaced the result is thiocarbamate).

Dithiocarbamate also refers to the dithiocarbamate ion and its salts. A common example is sodium diethyldithiocarbamate . Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber.

---

Formation Many secondary react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts:

Ammonia reacts with carbon disulfide similarly, to give ammonium dithiocarbamate:

Dithiocarbamate salts are pale colored solids that are soluble in water and Solvent.

---

Dithiocarbamic acid A primary amine and carbon disulfide react to give a dithiocarbamic acid:

In the presence of diimides or pyridine, these acids convert to :

---

Reactions Dithiocarbamates are readily S-alkylated. Thus, methyl dimethyldithiocarbamate can be prepared by methylation of the dithiocarbamate:

Oxidation of dithiocarbamates gives the thiuram disulfide:

Thiuram disulfides react with to give esters of dithiocarbamic acid:

Dithiocarbamates react with transition metal salts to give a wide variety of transition metal dithiocarbamate complexes.

---

Structure and bonding Dithiocarbamates are described by invoking resonance structures that emphasize the pi-donor properties of the amine group. This bonding arrangement is indicated by a short C–N distance and the coplanarity of the core as well as the atoms attached to N.

Dimitri Coucouvanis (1979). 9780470166277 ISBN 9780470166277

Because of the pi-donation from nitrogen, dithiocarbamates are more basic than structurally related anions such as dithiocarboxylates and . Consequently, they tend to bind as bidentate ligands. Another consequence of the C–N multiple bonding is that rotation about that bond is subject to a high barrier.

---

Applications Several transition metal dithiocarbamate complexes are useful in industry. Zinc dithiocarbamates are used to modify the of certain with sulfur, a process called vulcanization. They are used as ligands for chelating metals.

Some dithiocarbamates, specifically ethylene bisdithiocarbamates (), in the form of complexes with manganese (maneb), zinc (zineb) or a combination of manganese and zinc (mancozeb), have been used extensively as fungicides in agriculture since the 1940s. In the United States they began to be registered for use in the late 1950s and early 1960s and were quickly put to work on sooty blotch and flyspeck. Many growers switched from captan to EBDCs for the longer residual period. Both captan and EBDCs were the primary treatments for SBFS in that country until the early 1990s when the US Environmental Protection Agency banned EBDCs within 77 days to harvest. This effectively made summer use impossible, reduced EBDC use overall, and radically increased SBFS.

---

See also

• Xanthate

Post Comment