We
can say that Tetrahydroisoquinoline is a
weaker base than Tetrahydroquinoline because the electron pair on nitrogen of Tetrahydroisoquinoline
is strongly held by virtue of being delocalized into the π system of the aromatic
ring. The unshared pair in Tetrahydroquinoline is localized on nitrogen, less strongly
held, and therefore “more available” in an acid–base reaction.
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