Quinoline is less basic than pyridine, even though it has more resonating structures. Why? Does the negative inductive effect reduce basicity of quinoline?
This is not due to the inductive effect, but rather, due to solvation. The positive charge of quinoline on the nitrogen is harder to solvate due to steric repulsion of the nearby ring, whereas in pyridine, the small hydrogen atoms in place do not pose a strong steric hindrance for the solvation of the ion.