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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Lo.Lee.Ta. on September 01, 2013, 05:32:06 PM

Title: How is this molecule non-aromatic? Seems like it's anti-aromatic... :/
Post by: Lo.Lee.Ta. on September 01, 2013, 05:32:06 PM

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi1261.photobucket.com%2Falbums%2Fii596%2Flolita56381%2Fchem2212p3_zps3bfe4e87.jpg&hash=31b905e9a36f7c3eb12374c4be55a0b6db4516fc)


It looks to me like each ring has 4 pi electrons, so it follows the 4n rule for being anti-aromatic.

It also looks like it's planar...


So, why is this molecule non-aromatic?

Thanks for the help.  :)

Title: Re: How is this molecule non-aromatic? Seems like it's anti-aromatic... :/
Post by: Corribus on September 01, 2013, 05:45:51 PM

First of all, polycyclic systems don't always follow Huckel's rule.  Second, there are two sp3 hybridized carbons that prevent resonance stabilization.