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Tuesday, November 19, 2019

Basicity of Guanidine :

Guanidine is strongest organic nitrogenous compound with the formula HNC(NH2)2. Guanidine is analogue of carbonic acid. That is, the C=O group in carbonic acid is replaced by a C=NH group, and each OH is replaced by a NH2 group.

A guanidine group also appears in larger organic molecules, including on the side chain of arginine (a basic amino acid).

It is a colourless solid that dissolves in polar solvents. It is a strong base that is used in the production of plastics and explosives. It is found in urine as a normal product of protein metabolism.

Basicity of Guanidine:
Guanidine is the strongest base among neutral compounds:

The remarkable basicity of guanidine is attributed to the fact that the positive charge on
the guanidinium ion is delocalized equally over the three nitrogen atoms, as shown by
these three equivalent resonating  structures:

Basicity of nitrogen can be increased by attachment to pi-donors (NH2) group. These two pi-donating NH2 groups donate electron density to the (pi-accepting) C=NH. Hence, the guanidinium ion is a highly stable cation.

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