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- Cyclodecapentaene abstract "Cyclodecapentaene or [10]annulene is an annulene with molecular formula C10H10. This organic compound is a conjugated 10 pi electron cyclic system and according to Huckel's rule it should display aromaticity. It is not aromatic, however, because of a combination of steric strain and angular strain. The planar all-cis isomer (1) (like benzene is) would have bond angles of 144° which creates large amounts of bond strain relative to the ideal 120° for sp2 hybridization. A boat-like all-cis conformation (2) relieves much of the angular strain but is still unstable with respect to the next planar trans, cis, trans, cis, cis isomer (3). Yet this isomer suffers from steric repulsion between the two internal hydrogen atoms. The nonplanar trans, cis, cis, cis, cis isomer (4) is the most stable of all the possible isomers. The parent [10]annulene can be obtained by photolysis of cis-9,10-dihydronaphthalene as a mixture of isomers. Because of their lack in stability even at low temperatures the reaction products revert to the original dihydronaphthalene.Aromaticity can still be induced in [10]annulenes by fixation of the planar geometries and there exist two methods to bring it about. Replacing two hydrogen atoms by a methylene bridge (-CH2-) gives the planar bicyclic 1,6-methano[10]annulene (5). This compound is aromatic as judged from lack in bond length alternation by x-ray crystallography and a telltale diamagnetic ring current from NMR spectroscopy.A classical organic synthesis of this compound starts from a Birch reduction of naphthalene to tetrahydronaphthalene (or isotetralin), is followed by carbene addition of dichlorocarbene (prepared in-situ from chloroform and the potassium salt of tert-butanol) followed by a second organic reduction that removes the chloride substituents and is concluded by the organic oxidation by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ).Another way to restore aromaticity in [10]annulene by plane fixation is by incorporation of a methine bridge to a tricyclic[10]annulene core structure (6).2 When deprotonated to form the anion this type of compound is even more stabilized. The central carbanion makes the molecule even more planar and the number of resonance structures that can be drawn is extended to 7 included two resonance forms with a complete benzene ring. By computational chemistry it is demonstrated that the tricyclic[10]annulene derivative with an annulated benzene ring and a full set of cyano substituents (7) is one of the most acidic compounds known with a computed pKa in DMSO of - 30.4 (compared to for instance -20 for magic acid) 1.Azulene is also a 10 pi electron system in which aromaticity is maintained but in yet another way.".
- Cyclodecapentaene thumbnail 10-annulene.svg?width=300.
- Cyclodecapentaene wikiPageExternalLink prepContent.asp?prep=cv6p0731.
- Cyclodecapentaene wikiPageExternalLink article.asp?doi=b502006a.
- Cyclodecapentaene wikiPageExternalLink article.asp?doi=C39800000691.
- Cyclodecapentaene wikiPageID "2423647".
- Cyclodecapentaene wikiPageLength "4443".
- Cyclodecapentaene wikiPageOutDegree "52".
- Cyclodecapentaene wikiPageRevisionID "682511297".
- Cyclodecapentaene wikiPageWikiLink 1,6-Methano(10)annulene.
- Cyclodecapentaene wikiPageWikiLink 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone.
- Cyclodecapentaene wikiPageWikiLink 2,3-dichloro-5,6-dicyano-1,4-benzoquinone.
- Cyclodecapentaene wikiPageWikiLink Acid_dissociation_constant.
- Cyclodecapentaene wikiPageWikiLink Angular_strain.
- Cyclodecapentaene wikiPageWikiLink Anion.
- Cyclodecapentaene wikiPageWikiLink Annulated.
- Cyclodecapentaene wikiPageWikiLink Annulation.
- Cyclodecapentaene wikiPageWikiLink Annulene.
- Cyclodecapentaene wikiPageWikiLink Aromatic_ring_current.
- Cyclodecapentaene wikiPageWikiLink Aromaticity.
- Cyclodecapentaene wikiPageWikiLink Azulene.
- Cyclodecapentaene wikiPageWikiLink Bicyclic_molecule.
- Cyclodecapentaene wikiPageWikiLink Birch_reduction.
- Cyclodecapentaene wikiPageWikiLink Bond_angle.
- Cyclodecapentaene wikiPageWikiLink Bond_length.
- Cyclodecapentaene wikiPageWikiLink Bridge_(chemical).
- Cyclodecapentaene wikiPageWikiLink Carbanion.
- Cyclodecapentaene wikiPageWikiLink Carbene.
- Cyclodecapentaene wikiPageWikiLink Category:Annulenes.
- Cyclodecapentaene wikiPageWikiLink Chemical_formula.
- Cyclodecapentaene wikiPageWikiLink Chloroform.
- Cyclodecapentaene wikiPageWikiLink Cis_isomer.
- Cyclodecapentaene wikiPageWikiLink Cis–trans_isomerism.
- Cyclodecapentaene wikiPageWikiLink Computational_chemistry.
- Cyclodecapentaene wikiPageWikiLink Conjugated_system.
- Cyclodecapentaene wikiPageWikiLink Cyanide.
- Cyclodecapentaene wikiPageWikiLink Cyano.
- Cyclodecapentaene wikiPageWikiLink Cyclic_compound.
- Cyclodecapentaene wikiPageWikiLink Deprotonation.
- Cyclodecapentaene wikiPageWikiLink Diamagnetic_ring_current.
- Cyclodecapentaene wikiPageWikiLink Dichlorocarbene.
- Cyclodecapentaene wikiPageWikiLink Dimethyl_sulfoxide.
- Cyclodecapentaene wikiPageWikiLink Huckels_rule.
- Cyclodecapentaene wikiPageWikiLink Hxc3xbcckels_rule.
- Cyclodecapentaene wikiPageWikiLink Ion.
- Cyclodecapentaene wikiPageWikiLink Magic_acid.
- Cyclodecapentaene wikiPageWikiLink Methine.
- Cyclodecapentaene wikiPageWikiLink Methine_group.
- Cyclodecapentaene wikiPageWikiLink Methylene_bridge.
- Cyclodecapentaene wikiPageWikiLink Molecular_formula.
- Cyclodecapentaene wikiPageWikiLink Molecular_geometry.
- Cyclodecapentaene wikiPageWikiLink NMR_spectroscopy.
- Cyclodecapentaene wikiPageWikiLink Naphthalene.
- Cyclodecapentaene wikiPageWikiLink Nuclear_magnetic_resonance_spectroscopy.
- Cyclodecapentaene wikiPageWikiLink Organic_Syntheses.
- Cyclodecapentaene wikiPageWikiLink Organic_compound.
- Cyclodecapentaene wikiPageWikiLink Organic_oxidation.
- Cyclodecapentaene wikiPageWikiLink Organic_redox_reaction.
- Cyclodecapentaene wikiPageWikiLink Organic_reduction.
- Cyclodecapentaene wikiPageWikiLink Organic_synthesis.
- Cyclodecapentaene wikiPageWikiLink PKa.
- Cyclodecapentaene wikiPageWikiLink Photodissociation.
- Cyclodecapentaene wikiPageWikiLink Photolysis.
- Cyclodecapentaene wikiPageWikiLink Pi_bond.
- Cyclodecapentaene wikiPageWikiLink Pi_electron.
- Cyclodecapentaene wikiPageWikiLink Resonance_(chemistry).
- Cyclodecapentaene wikiPageWikiLink Resonance_structure.
- Cyclodecapentaene wikiPageWikiLink Ring_strain.
- Cyclodecapentaene wikiPageWikiLink Steric_strain.
- Cyclodecapentaene wikiPageWikiLink Substituent.
- Cyclodecapentaene wikiPageWikiLink Tert-Butanol.
- Cyclodecapentaene wikiPageWikiLink Tert-Butyl_alcohol.
- Cyclodecapentaene wikiPageWikiLink Van_der_Waals_strain.
- Cyclodecapentaene wikiPageWikiLink X-ray_crystallography.
- Cyclodecapentaene wikiPageWikiLink File:10-annulene.svg.
- Cyclodecapentaene wikiPageWikiLink File:Methanonaphtalene.gif.
- Cyclodecapentaene wikiPageWikiLinkText "Cyclodecapentaene".
- Cyclodecapentaene wikiPageWikiLinkText "[10]annulene".
- Cyclodecapentaene wikiPageWikiLinkText "cyclodecapentaene".
- Cyclodecapentaene hasPhotoCollection Cyclodecapentaene.
- Cyclodecapentaene wikiPageUsesTemplate Template:Annulenes.
- Cyclodecapentaene wikiPageUsesTemplate Template:Chem.
- Cyclodecapentaene subject Category:Annulenes.
- Cyclodecapentaene hypernym Annulene.
- Cyclodecapentaene type ChemicalCompound.
- Cyclodecapentaene type Cycloalkene.
- Cyclodecapentaene type Hydrocarbon.
- Cyclodecapentaene comment "Cyclodecapentaene or [10]annulene is an annulene with molecular formula C10H10. This organic compound is a conjugated 10 pi electron cyclic system and according to Huckel's rule it should display aromaticity. It is not aromatic, however, because of a combination of steric strain and angular strain. The planar all-cis isomer (1) (like benzene is) would have bond angles of 144° which creates large amounts of bond strain relative to the ideal 120° for sp2 hybridization.".
- Cyclodecapentaene label "Cyclodecapentaene".
- Cyclodecapentaene sameAs 사이클로데카펜타엔.
- Cyclodecapentaene sameAs m.07c1g8.
- Cyclodecapentaene sameAs Q5198692.
- Cyclodecapentaene sameAs Q5198692.
- Cyclodecapentaene wasDerivedFrom Cyclodecapentaene?oldid=682511297.
- Cyclodecapentaene depiction 10-annulene.svg.
- Cyclodecapentaene isPrimaryTopicOf Cyclodecapentaene.