Is thiophene an aromatic?

1 Answer
Ernest Z.
Apr 28, 2015

Yes, thiophene is an aromatic compound.

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

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

Pyrrole, furan, and thiophene are other aromatic compounds with #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"# is more electronegative than #"C"#.

#"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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