cyclobutadiene
Sign in to saveCyclobutadiene is an organic compound with the formula . It is very reactive owing to its tendency to dimerize. Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is quite stable. Since the compound degrades by a bimolecular process, the species can be observed by matrix isolation techniques at temperatures below 35 K. It is thought to adopt a rectangular structure.
Article
6 sectionsContents
- Structure and reactivity
- Synthesis
- Trapping
- See also
- References
- Further reading
Cyclobutadiene is an organic compound with the formula . It is very reactive owing to its tendency to dimerize. Although the parent compound has not been isolated, some substituted derivatives are robust and a single molecule of cyclobutadiene is quite stable. Since the compound degrades by a bimolecular process, the species can be observed by matrix isolation techniques at temperatures below 35 K. It is thought to adopt a rectangular structure.
==Structure and reactivity== The compound is the prototypical antiaromatic hydrocarbon with 4 π electrons. It is the smallest [n]-annulene ([4]-annulene). Its rectangular structure is the result of a pseudo- (or second order) Jahn–Teller effect, which distorts the molecule and lowers its symmetry, converting the triplet to a singlet ground state. The electronic states of cyclobutadiene have been explored with a variety of computational methods. The rectangular structure is consistent with the existence of two different 1,2-dideutero-1,3-cyclobutadiene valence isomers. This distortion indicates that the pi electrons are localized, in agreement with Hückel's rule which predicts that a π-system of 4 electrons is not aromatic.