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Antiaromaticity is a chemical property of a cyclic molecule with a π electron system that has higher energy, i.e., it is less stable due to the presence of 4n delocalised (π or lone pair) electrons in it, as opposed to aromaticity. Unlike aromatic compounds, which follow Hückel's rule ([4n+2] π electrons) and are highly stable, antiaromatic compounds are highly unstable and highly reactive. To avoid the instability of antiaromaticity, molecules may change shape, becoming non-planar and therefore breaking some of the π interactions. In contrast to the diamagnetic ring current present in aromatic compounds, antiaromatic compounds have a paramagnetic ring current, which can be observed by NMR spectroscopy. Examples of antiaromatic compounds are pentalene (A), biphenylene (B), cyclopentadienyl cation (C). The prototypical example of antiaromaticity, cyclobutadiene, is the subject of debate, with some scientists arguing that antiaromaticity is not a major factor contributing to its destabilization. Cyclooctatetraene is an example of a molecule adopting a non-planar geometry to avoid the destabilization that results from antiaromaticity. If it were planar, it would have a single eight-electron π system around the ring, but it instead adopts a boat-like shape with four individual π bonds. Because antiaromatic compounds are often short-lived and difficult to work with experimentally, antiaromatic destabilization energy is often modeled by simulation rather than by experimentation. The term 'antiaromaticity' was first proposed by Ronald Breslow in 1967 as "a situation in which a cyclic delocalisation of electrons is destabilising". The IUPAC criteria for antiaromaticity are as follows: The molecule must be cyclic. The molecule must be planar. The molecule must have a complete conjugated π-electron system within the ring. The molecule must have 4n π-electrons where n is any integer within the conjugated π-system. This differs from aromaticity only in the fourth criterion: aromatic molecules have 4n +2 π-electrons in the conjugated π system and therefore follow Hückel’s rule.

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Cyclooctatetraene

1,3,5,7-Cyclooctatetraene (COT) is an unsaturated derivative of cyclooctane, with the formula C8H8. It is also known as [8]annulene. This polyunsaturated hydrocarbon is a colorless to light yellow flammable liquid at room temperature. Because of its stoichiometric relationship to benzene, COT has been the subject of much research and some controversy. Unlike benzene, C6H6, cyclooctatetraene, C8H8, is not aromatic, although its dianion, C8H82- (cyclooctatetraenide), is. Its reactivity is characteristic of an ordinary polyene, i.

Hückel's rule

In organic chemistry, Hückel's rule predicts that a planar ring molecule will have aromatic properties if it has 4n + 2 π electrons, where n is a non-negative integer. The quantum mechanical basis for its formulation was first worked out by physical chemist Erich Hückel in 1931. The succinct expression as the 4n + 2 rule has been attributed to W. v. E. Doering (1951), although several authors were using this form at around the same time.

Antiaromaticity

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