Question

Guanidine is a stronger base than the typical amine. Explain the factors contributing to the increased basicity of guanidine compared to other amines.

Answer 1

Guanidine's increased basicity compared to other amines is due to the effective delocalization of positive charge across its three nitrogen atoms when forming its conjugate acid, providing exceptional stabilization.

Step-by-step explanation:

Guanidine is a stronger base than most amines because of its ability to delocalize the positive charge across three nitrogen atoms when it accepts a proton. In other amines, such as CH3NH2 (methylamine) and (CH3)2NH (dimethylamine), the electron density is localized on the nitrogen, and there is less stabilization when they form their respective conjugate acids.

For example, the conjugate acid of methylamine (CH3NH3+) cannot distribute the positive charge as effectively as guanidine can. This charge distribution in guanidine greatly stabilizes the conjugate acid form, making guanidine a stronger base compared to other amines.