Could someone please help me with the following question: Rank each compound in terms of increasing basicity: aniline, pyrrole, pyridine. The answer is:
pyrrole < aniline < pyridine. What is the logic behind this ranking? Why is aniline a weaker base than pyridine? I thought that aniline's lone pair
of electrons is in a sp^3 orbital while pyridine's is in a sp^2 orbital... so wouldn't pyridine's electrons be more tightly held due to the higher
s character and therefore be a weaker base than aniline? Why is this reasoning wrong? If anyone could help me with this, it would be much appreciated! Thank
you!