Is Cyclopropenone Aromatic or Not?

Chemistry
Is cyclopropenone aromatic? Before reading on, try to anticipate the answer to that question. When most students think of aromatic, they think of simple hydrocarbons—compounds composed of hydrogen and carbon atoms only. The best known example of an aromatic hydrocarbon is the 6-sided cyclic compound benzene—C₆H₆. Benzene, if drawn according to classical structures, has alternating single and double bonds between carbon atoms. Basic Qualifications for Aromaticity A double bond consists of one sigma (σ) and one pi (π) bond. If the ring is single rather than multiple (as, for instance, for naphthalene, which is comprised of two fused rings), and if it has 4n+2 completely conjugated π electrons in a closed loop or ring, is neutral, and is flat, the structure obeys Hückel’s rule and will be aromatic. There are…
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Aromatic Tropylium Ion

Chemistry
[caption id="attachment_20212" align="alignright" width="440"] Aromatic tropylium cation[/caption] Aromatics are separate category of organic compounds. Often aromatic compounds are electrically neutral. However, a few do carry a charge. They are ions.¹ In fact many aromatic ions would not be aromatic if they lost their charge. We will consider the aromatic tropylium cation in this article. Three Carbon Atoms The smallest aromatic ion is the cyclopropenyl cation. The neutral cyclopropene molecule possesses 4 π-electrons. That is not an aromatic number. By making it a cation, it loses 2 of them, meeting the qualification for aromatic compounds.¹ [caption id="attachment_16191" align="alignright" width="240"] Spacefill Model.[/caption] Four Carbon Atoms On the basis of π-electron count alone, one might suppose a cyclobutadienyl di-anion or a cyclobutadienyl di-cation, would display aromaticity. That is not the case. There are…
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