Tuesday, January 22, 2019

organic chemistry - Is biphenyl considered to be aromatic?


1,1'-biphenyl


Biphenyl has 12 π-electrons and according to Hückel’s rule, it should not be aromatic because $12 \neq 4n+2$, but it nevertheless is aromatic. Why is that so?



Answer



The two rings in biphenyl are inclined at an angle of 44° to each other because of the large steric repulsion between the ortho hydrogens on each ring.


enter image description here


For Hückel's rule to be applied, the molecule must be able to be planar and it must be monocyclic.



Due to the molecule not being planar, the two rings are not strongly conjugated to each other and you cannot apply Hückel's rule to the whole system. Additionally, the whole system is not monocyclic. Hückel's rule can be applied to each ring individually and they are both aromatic.


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