Why is benzene more aromatic than thiophene, furan and pyrrole?
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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.
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Explanation:
Benzene is the archetypical aromatic compound. It is planar, bond angles=120º, all carbon atoms in the ring are sp2 hybridized, and the pi-orbitals are occupied by 6 electrons. The aromatic heterocycle pyridine is similar to benzene, and is often used as a weak base for scavenging protons. Furan and pyrrole have heterocyclic five-membered rings, in which the heteroatom has at least one pair of non-bonding valence shell electrons. By hybridizing this heteroatom to a sp2 state, a p-orbital occupied by a
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