Dithiocarbamate
salt or ester of any dithiocarbamic acid
In organic chemistry, a dithiocarbamate is a chemical compound with the general formula R2N−C(=S)−S−R. It contains the functional group with the structure >N−C(=S)−S−. 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 R2N−CS−2 and its salts. A common example is sodium diethyldithiocarbamate (CH3CH2)2N−CS−2Na+. Dithiocarbamates and their derivatives are widely used in the vulcanization of rubber.
Formation
Many secondary amines react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts:
R2NH + CS2 + NaOH → R2NCS−2Na+ + H2O
Ammonia reacts with CS2 similarly, to give ammonium dithiocarbamate:
2 NH3 + CS2 → H2N−CS−2[NH4]+
Dithiocarbamate salts are pale colored solids that are soluble in water and polar organic solvents.
Dithiocarbamic acid
A primary amine and carbon disulfide react to give a dithiocarbamic acid:
RNH2 + CS2 → R(H)N−CS2H
In the presence of diimides or pyridine, these acids convert to isothiocyanates:
R(H)N−CS2H + C(=N−R')2 → R−N=C=S + S=C(−NHR')2
Reactions
Dithiocarbamates are readily S-alkylated. Thus, methyl dimethyldithiocarbamate can be prepared by methylation of the dithiocarbamate:
(CH3)2NCS2Na + (CH3O)2SO2 → (CH3)2NC(S)SCH3 + Na[CH3OSO3]
Oxidation of dithiocarbamates gives the thiuram disulfide:
2 R2NCS−2 → [R2NC(S)S]2 + 2 e−
Thiuram disulfides react with Grignard reagents to give esters of dithiocarbamic acid:
[R2NC(S)S]2 + R'MgX → R2NC(S)SR' + R2NCS2MgX
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 NCS2 core as well as the atoms attached to N.
Because of the pi-donation from nitrogen, dithiocarbamates are more basic than structurally related anions such as dithiocarboxylates and xanthates.
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