page_title: Antiaromaticity
section_title: Cyclobutadiene
hierarchical_section_title: Antiaromaticity / Examples / Cyclobutadiene
caption_attribution_description: English: Cyclobutadiene
context_page_description: Antiaromaticity is a characteristic of a cyclic molecule with a π electron system that has higher energy due to the presence of 4n delocalised electrons in it. Unlike aromatic compounds, which follow Hückel's rule 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, biphenylene, cyclopentadienyl cation. 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.
context_section_description: Cyclobutadiene is a classic textbook example of an antiaromatic compound. It is conventionally understood to be planar, cyclic, and have 4 π electrons (4n for n=1) in a conjugated system.
  However, it has long been questioned if cyclobutadiene is genuinely antiaromatic and recent discoveries have suggested that it may not be.  Cyclobutadiene is particularly destabilized and this was originally attributed to antiaromaticity. However, cyclobutadiene adopts more double bond character in two of its parallel bonds than others and the π electrons are not delocalized between the two double-bond-like bonds, giving it a rectangular shape as opposed to a regular square. As such, cyclobutadiene behaves like two discrete alkenes joined by two single bonds, and is therefore non-aromatic rather than antiaromatic.
  Despite the lack of this π-antiaromatic destabilization effect, none of its 4n π-electron relatives (cyclooctatetraene, etc.) had even close to as much destabilization, suggesting there was something more going on in the case of cyclobutadiene. It was found that a combination of angle strain, torsional strain, and Pauli repulsion leads to the extreme destabilization experienced in this molecule.
  This discovery is awkward in that it contradicts basic teachings of antiaromaticity. At this point of time, it is presumed that cyclobutadiene will continue to be used to introduce the concept of antiaromaticity in textbooks as a matter of convenience, even though classifying it as antiaromatic technically may not be accurate.
caption: Cyclobutadiene
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