Saturday, 11 June 2016

organic chemistry - Are the following compounds aromatic?



Structures in question


I know Huckel's rule states that an aromatic species must have $4n+2$ π-electrons. Is the last molecule also aromatic?



Answer



Molecule 1, the cyclopentadienyl cation, is not aromatic. It only has 4 π electrons and does not fit the $4n+2$ rule.


Molecule 2, the cycloheptatrienyl cation (or tropylium cation), is aromatic; it has 6 π electrons and fits the $4n+2$ rule with $n=1$.


Molecule 3, azulene, is generally considered to be aromatic. It fits the $4n+2$ rule with $n=2$, and is often referred to as a "nonbenzenoid" aromatic compound. It can also be viewed as a fusion of two other aromatic units, the tropylium cation and the cyclopentadienyl anion.


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