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Why is pyridine a poor nucleophile?

Answer 1

Pyridine is neither a strong base nor a strong nucleophile. As a physical scientist you should look at the appropriate data.

In comparison to similar secondary ammonium salts, the acidity of the pyridinium cation is significantly higher, and the lone pair on nitrogen is somewhat delocalized around the ring.

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Answer 2

Santiago Alfonso

Pyridine is a poor nucleophile because its nitrogen lone pair is involved in resonance stabilization with the aromatic ring, making it less available for nucleophilic attack. Additionally, pyridine's lone pair is less reactive compared to other nitrogen-containing compounds due to its lower electron density caused by resonance effects.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.