March 29, 2024, 07:16:46 AM
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Topic: Can Frost Circle (Huckle Rule) be applied to fused aromatic ring systems?  (Read 1598 times)

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Offline darkdevil

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According to Hückel's rule, an aromatic compound must have (4n + 2) π electrons

However, most examples showed in textbooks only demonstrated simple aromatic compounds such as benzene. I wonder if the Frost Circle rule can be applied to heterocyclics such as indoles or other fused ring systems? and how do you draw the Frost Circle of them? which vertex to choose as the bottom orbital?

Thanks!!!

Offline sjb

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I think probably not, at least not simply. One of the simplifications I think Frost Muslin(?) diagrams imply is that the molecule in question is fairly highly symmetric, so would not work for e.g. indole, let alone things like thiophene or imidazole.

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