Four nitrogen compounds are shown beside the options (the drawn compound is pyrimidine, for reference). Which structure is the strongest base?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: A

Piperidine (pKaH about 11.1) has an sp3 nitrogen with an available localised lone pair and +I alkyl groups. Pyridine (5.2), aniline (4.6) and pyrrole (about -3.8, lone pair part of the aromatic sextet) are weaker.

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