Is thiophene an aromatic?

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Is thiophene an aromatic?

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Answer 1 · 2015-04-28T21:37:24

Yes, thiophene is an aromatic compound.

According to Hückel's rule, a planar, conjugated, cyclic molecule is aromatic if it has $4 n + 2$ $4n+2$ π electrons. The value of $n$ $n$ can be zero or any positive integer.

The most common aromatic molecule is benzene ( $n = 1$ $n =1$ ).

Pyrrole, furan, and thiophene are other aromatic compounds with $n = 1$ $n =1$ .

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The heteroatoms each contribute two electrons to the π system.

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However, the resonance stabilization in thiophene (122 kJ/mol) is less than that in benzene (152 kJ/mol), because $S$ $"S"$ is more electronegative than $C$ $"C"$ .

$S$ $"S"$ is less "willing" to donate its electrons to the aromatic system.

But, because thiophene is aromatic, it does not have the properties of ordinary thioethers.

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Is thiophene an aromatic?

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