Question

Pyridine is less basic than triethylamine because

Answer 1

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Triethylamine is a stronger basethan Pyridine and the ionic form is stablized. ... Therefore nucleus of Nitrogen atom has stonger attraction for electrons in pyridinethat means it is less available for coordination with a protons compared to Et3N electron pair. Thus pyridine is a weak base.

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Answer 2

Triethyl amime is more basic as the lone pair on the N atom in case of pyridine will be involved in resonance with the ring while the C2H5- groups on triethyl amine show +I nature and increase the ability of the N atom to give out electrons