The remarkable basicity of guanidine

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.

Related Questions:

1. How is base strength related to the availabihty of the electron-pair?
2. Amines are more basic than ammonia why?
3. What is relative basic strength order 1° amines , 2°amines and 3° amines ? Explain:
4. Give an explanation for the fact that Guanidine NH=C(CH3)2 is a stronger base than most of amines?
5. Arrange in correct order of basic Character of aniline, pyrrol, pyridine and piperidine?
6. What is correct basicity order of pyridine, pyridazine, pyrimidine and pyrazine ?
7. Give an explanation for the fact that Guanidine NH=C(CH3)2 is a stronger base than most of amines?
8. Arrange in correct order of basic Character of aniline, pyrrol, pyridine and piperidine?
9. What is correct basicity order of pyridine, pyridazine, pyrimidine and pyrazine ?
10. Why pyridine is more basic than Pyrrole?
11. Why pyrimidine is less basic than pyridine?
12. Imidazole is more basic than pyridine? Why?
13. Biological Important of Imidazole and structure:
14. Pyridine is almost 1 million times less basic than piperidine? Why?
15. Cyclohexylamine amine is the stronger base than Aniline? Why?
16. Tetrahydroquinoline amine is the stronger base than Tetrahydroisoquinoline? Why?
17. Arrange the following in the order of increasing basicity : p-Toluidine, N, N-Dimethyl-p-toluidine, p-Nitroaniline, Aniline. (I.I.T.1986)
18. Arrange the following in the increasing order of their acid strength : Methyl amine, Dimethyl amine, Aniline, N-methyl aniline (I.I.T, 1988).