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- Cyclobutadiene abstract "Cyclobutadiene is the smallest [n]-annulene ([4]-annulene), an extremely unstable hydrocarbon having a lifetime shorter than five seconds in the free state[citation needed]. It has chemical formula C4H4. It is believed to be in equilibrium between a pair of rectangular/nonplanar ground states and a square, excited triplet state based upon theoretical calculations, and through spectroscopic and crystallographic investigation of substituted cyclobutadienes, in an argon matrix[citation needed] and inside carceplexes. Though it has alternating single and double bonds, it is predicted triplet, unstable and antiaromatic by Hückel's rule, because its ring has 4 π-electrons, and 4 is not twice an odd number. Some cyclobutadiene–metal compounds are stable, thought to be caused by the metal atom providing 2 more electrons to the system. Nonplanar, rectangular distortion to a singlet ground state is caused by the Jahn–Teller effect. Tetra-t-butyl substituted cyclobutadiene is sufficiently stable to gather x-ray crystallographic images of the structure which has a distorted, nonplanar configuration and double bond lengths longer than normal (1.464 vs expected 1.34)The pi electron energy of cyclobutadiene is higher than that of its open-chain counterpart, 1,3-butadiene, and it is therefore said to be anti-aromatic rather than aromatic. The electronic states of cyclobutadiene have been explored with a variety of computational methods. The singlet ground state has a rectangular structure. The first excited state is a triplet with a square geometry. The rectangular structure is consistent with the existence of two different 1,2-dideuterio-1,3-cyclobutadiene stereoisomers. This indicates that the pi electrons are localized and therefore not considered to be aromatic. Cyclobutadiene is far from stable, it is highly reactive and has a very short lifetime. Cyclobutadiene dimerizes by a Diels-Alder reaction at 35 K[citation needed]. The monomeric form has been studied at higher temperatures by trapping with matrix isolation in a noble gas[citation needed].".
- Cyclobutadiene iupacName "1,3-Cyclobutadiene".
- Cyclobutadiene thumbnail Cyclobutadiene_structure.svg?width=300.
- Cyclobutadiene wikiPageID "843920".
- Cyclobutadiene wikiPageRevisionID "585189280".
- Cyclobutadiene hasPhotoCollection Cyclobutadiene.
- Cyclobutadiene imagefilel "Cyclobutadiene structure.svg".
- Cyclobutadiene imagefiler "Cyclobutadiene3D.png".
- Cyclobutadiene imagenamel "Cyclobutadiene".
- Cyclobutadiene imagesizel "100".
- Cyclobutadiene imagesizer "120".
- Cyclobutadiene iupacname "13".
- Cyclobutadiene name "Cyclobutadiene".
- Cyclobutadiene othernames "Cyclobutadiene".
- Cyclobutadiene othernames "[4]Annulene".
- Cyclobutadiene verifiedrevid "443547917".
- Cyclobutadiene subject Category:Annulenes.
- Cyclobutadiene subject Category:Antiaromatic_compounds.
- Cyclobutadiene type Abstraction100002137.
- Cyclobutadiene type AntiaromaticCompounds.
- Cyclobutadiene type Cognition100023271.
- Cyclobutadiene type Compound105870180.
- Cyclobutadiene type Concept105835747.
- Cyclobutadiene type Content105809192.
- Cyclobutadiene type Idea105833840.
- Cyclobutadiene type PsychologicalFeature100023100.
- Cyclobutadiene type Whole105869584.
- Cyclobutadiene type ChemicalCompound.
- Cyclobutadiene type ChemicalSubstance.
- Cyclobutadiene type ChemicalSubstanceType.
- Cyclobutadiene type ChemicalObject.
- Cyclobutadiene type Thing.
- Cyclobutadiene comment "Cyclobutadiene is the smallest [n]-annulene ([4]-annulene), an extremely unstable hydrocarbon having a lifetime shorter than five seconds in the free state[citation needed]. It has chemical formula C4H4.".
- Cyclobutadiene label "Ciclobutadiene".
- Cyclobutadiene label "Ciclobutadieno".
- Cyclobutadiene label "Cyclobutadieen".
- Cyclobutadiene label "Cyclobutadien".
- Cyclobutadiene label "Cyclobutadiene".
- Cyclobutadiene label "Cyclobutadiène".
- Cyclobutadiene label "Циклобутадиен".
- Cyclobutadiene label "حلقي البوتادين".
- Cyclobutadiene label "シクロブタジエン".
- Cyclobutadiene label "环丁二烯".
- Cyclobutadiene sameAs Cyclobutadien.
- Cyclobutadiene sameAs Κυκλοβουταδιένιο.
- Cyclobutadiene sameAs Cyclobutadiène.
- Cyclobutadiene sameAs Ciclobutadiene.
- Cyclobutadiene sameAs シクロブタジエン.
- Cyclobutadiene sameAs 사이클로뷰타다이엔.
- Cyclobutadiene sameAs Cyclobutadieen.
- Cyclobutadiene sameAs Ciclobutadieno.
- Cyclobutadiene sameAs m.03gbp4.
- Cyclobutadiene sameAs Q415302.
- Cyclobutadiene sameAs Q415302.
- Cyclobutadiene sameAs Cyclobutadiene.
- Cyclobutadiene wasDerivedFrom Cyclobutadiene?oldid=585189280.
- Cyclobutadiene depiction Cyclobutadiene_structure.svg.
- Cyclobutadiene isPrimaryTopicOf Cyclobutadiene.
- Cyclobutadiene name "Cyclobutadiene".
