Dithiocarbamate

[1] Many secondary amines react with carbon disulfide and sodium hydroxide to form dithiocarbamate salts:[2] Ammonia reacts with CS2 similarly: Dithiocarbamate salts are pale colored solids that are soluble in water and polar organic solvents.

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.[6] Because of the pi-donation from nitrogen, dithiocarbamates are more basic than structurally related anions such as dithiocarboxylates and xanthates.

Zinc dithiocarbamates are used to modify the crosslinking of certain polyolefins with sulfur, a process called vulcanization.

[8] 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.

General chemical structure of dithiocarbamate esters. R and R" is any group (typically hydrogen or organyl ), and R' is organyl.
Main resonance structures of a dithiocarbamate anion.
Structure of the dimethyldithiocarbamate of zinc.
Methylenebis(dibutyldithiocarbamate) is an additive in some extreme pressure gear oils , serving as an antioxidant and protecting metal surfaces. [ 10 ]