2-Cyanoguanidine
2-Cyanoguanidine is a nitrile derived from guanidine. It is a dimer of cyanamide, from which it can be prepared. 2-Cyanoguanidine is a colourless solid that is soluble in water, acetone, and alcohol, but not nonpolar organic solvents.Production and use
2-Cyanoguanidine is produced by treating cyanamide with base. It is produced in soil by decomposition of cyanamide. A variety of useful compounds are produced from 2-cyanoguanidine, guanidines and melamine. For example, acetoguanamine and benzoguanamine are prepared by condensation of cyanoguanidine with the nitrile:
Cyanoguanidine is also used as a slow fertilizer. Formerly, it was used as a fuel in some explosives. It is used in the adhesive industry as a curing agent for epoxy resins.Chemistry
Two tautomeric forms exist, differing in the protonation and bonding of the nitrogen to which the nitrile group is attached.
2-Cyanoguanidine can also exist in a zwitterionic form via a formal acid–base reaction among the nitrogens.
Loss of ammonia from the zwitterionic form, followed by deprotonation of the remaining central nitrogen atom, gives the dicyanamide anion, −.
