| 词条 | Calicene |
| 释义 |
| ImageFile = Calicene.svg | ImageSize = 200px | IUPACName = 5-(2-Cyclopropen-1-ylidene)-1,3-cyclopentadiene | OtherNames = Triapentafulvalene | Section1 = {{Chembox Identifiers | CASNo = 6249-23-6 | PubChem = 12302244 | ChemSpiderID = 26537418 | SMILES = C1(C=CC=C1)=C2C=C2 | StdInChI= 1S/C8H6/c1-2-4-7(3-1)8-5-6-8/h1-6H | StdInChIKey = ZXWMPJFQZJXFQN-UHFFFAOYSA-N | Section2 = {{Chembox Properties | C=8|H=6 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = | Section3 = {{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} Calicene or Triapentafulvalene is a hydrocarbon of the fulvalene class with chemical formula C8H6, composed of linked a cyclopentadiene ring and a cyclopropene ring. PropertiesVery high resonance energy is predicted by Hückel method,[1] however its resonance energy is not high. The central double bond is polarized with a partial positive charge on the carbon atom of triangular ring and a partial negative charge on the carbon atom of pentagonal ring, in keeping with added Hückel's rule stability of rings containing 2 π electrons and 6 π electrons respectively. Calicene's dipole moment has been computed to be 4.66 D.[2] Several compounds that contains two or more calicene subunits are aromatic, such as trans-bicalicene[2](ring compound) or poly-2,7-[N]calicenes (chain compound)[3] Despite several attempts to prepare it, the parent calicene has so far defied attempts at synthesis.[4] However, 1,2,3,4,5,6-hexaphenylcalicene has been prepared and an experimental dipole moment of 6.3 D was measured.[5] References1. ^{{cite journal | last = Schaad| first = L. J. | author2 = B. Andes Hess , Jr |title = Dewar Resonance Energy | journal = Chem. Rev. | year = 2001 | volume = 101 | issue = 5 | pages = 1465–1476 | doi = 10.1021/cr9903609 |bibcode = |url = }} {{Hydrocarbon-stub}}2. ^1 {{cite journal | last = Oziminski | first = W. P. | author2 = M. Palusia |title = Capturing the elusive aromaticity of bicalicene | journal = Phys. Chem. Chem. Phys. | year = 2013 | volume = 15 | issue = | pages = 3286–3293| doi = 10.1039/C2CP43426A |bibcode = |url = }} 3. ^{{cite journal | last = Ratanadachanakin | first = Thawalrat | author2 = Collier, Willard E. r |title = Aromaticity of a series of poly-2,7-[N]calicenes| journal = Maejo International Journal of Science and Technology | year = 2015 | volume = | issue = 9.1 | pages = 21–31| doi = |bibcode = |url = http://www.mijst.mju.ac.th/vol9/21-31.pdf }} 4. ^{{Cite book|title=Houben-Weyl Methods of Organic Chemistry Vol. E 17d, 4th Edition Supplement: Carbocyclic Three-Membered Ring Compounds, Cyclopropenes, Author Index, Compound Index|last=de Meijere|first=Armin|publisher=Georg Thieme Verlag|year=2014|isbn=313181974X|location=Stuttgart|pages=2967}} 5. ^{{Cite journal|last=Agranat|first=Israel|last2=Bergmann|first2=Ernst D.|date=1965-01-01|title=Hexaphenyltriapentafulvalene|url=https://pubs.rsc.org/en/content/articlelanding/1965/c1/c19650000512|journal=Chemical Communications (London)|language=en|volume=0|issue=21|pages=512–513|doi=10.1039/C19650000512|issn=0009-241X}} 3 : Polycyclic nonaromatic hydrocarbons|Fulvalenes|Cyclopropenes |
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