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Aromatic Compounds and Cycloheptatrienyl

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Explain the following: a.) The cycloheptatrienyl anion is antiaromatic, whereas the cyclononatetraenyl anion is planar (in spite of the angle stain involved) and appears to be aromatic. b.) Although [16] annulene is not aromatic, it adds two electrons readily to form an aromatic dianion.

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The cycloheptatrienyl anion has 8Pi electrons as shown via Frost's circle (or the polygon rule). The two non-bonding electrons in this anion would be unhybridized leading to 2 more Pi electrons plus the 6Pi electrons from the 3 double bonds. Huckel's rule of ...

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This solution includes explanation and structural drawings in an attached Word document. 180 words.