Question

Why thiophene is more aromatic than furan and pyrrole?

Answer 1

Since N is less electronegative than O, it will be slightly more stable than O with that positive charge. Hence,pyrrole will be more aromatic than furan. Therefore, according to me, the aromaticity order should be: benzene > pyridine > pyrrole > furan > thiophene. But it is obviously wrong.
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Answer 2

Answer:

The aromaticity is ordered as Thiophene > Pyrrole > Furan.

Explanation:

Atoms with a more elevated electronegativity have their sole electron pair more tightly, decreasing the comfort of delocalization (aroma). Therefore, the multiple electronegative heteroatoms in furan decline aromaticity the most. Raising the electronegative S in Thiophene will guide to the most significant growth in aromaticity.

The aromaticity order in these heterocycles depends on the electronegativity of the heteroatom : 0>N>S Hence, the aromaticity is ordered as Thiophene > Pyrrole > Furan.

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