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Which N - atom of guanidine (H(2)overset...

Which N - atom of guanidine `(H_(2)overset(* *)(N)-overset(overset(* *)NH_(2))overset(|)(C)=overset(* *)(N)H)` is more basic and why?

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Protonation on the doubly bonded N - atoms produces a cation (conjugate acid) which is stabilised by resonance involving three equivalent canonical forms. On the other hand protonation on either of the singly bonded N - atoms produces a cation (conjugate acid) which is not stabilised by resonance. Thus the doubly bonded N - atom of guanidine is more basic.
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