14.3: Heteroaromaticity

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Jan 4, 2023
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- 14.2: Frost's Circle
- 15: Aromatic Substitution

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Aromaticity can also occur when atoms other than carbon are present in the ring. Pyridine is a good example. The nitrogen in pyridine is sp² hybridized, where the sp² orbital contains the lone pair and the atomic p orbital contains a single electron that is pairing with another electron in an atomic p orbital to create a $π$ bond. The aromatic stabilization energy for pyridine is 32 kcal/mol (much less than benzene). Heteroaromatics are higher in energy than benzene. Think of it this way – heteroatoms do not like sharing their electrons because they are more electronegative.

Screen Shot 2022-12-29 at 10.21.46 AM.png

How about other aromatics?

Screen Shot 2022-12-29 at 10.21.51 AM.png

Here is some additional nomenclature to learn:

Screen Shot 2022-12-29 at 10.22.00 AM.png

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