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- Annulyne abstract "Annulynes or 1,2-didehydroannulenes are conjugated monocyclic hydrocarbons with alternating alkene bonds in addition to at least one alkyne bond. They are related to annulenes who have just alternating double bonds. The smallest member of this class is [4]annulyne but is never observed because the molecule carries too much angle strain. The next member is [6]annulyne or benzyne which is a reactive intermediate well known in organic chemistry. [8]annulyne is known to exist but quickly dimerizes or trimerizes; the compound has been trapped as its radical anion and observed by EPR spectroscopy. [10]annulyne, like [4]annulyne, only exists in theory.[12]annulyne has been observed in 2005 by Stevenson et al. in solution by NMR spectroscopy at room temperature. Reaction of 1,5-hexadiyne and potassium tert-butoxide was reported to yield two isomers 5,9-di-trans-[12]-annulyne and 3,11-di-trans-[12]annulyne in a 1:1 ratio. The proposed reaction sequence involved an unspecified electron transfer reaction. A third single isomer 3,9-Di-trans-[12]annulyne could be obtained in three steps from hexabromocyclododecane. Unlike other annulynes, the [12]annulyne isomers were found to be very stable and did not self-condense. These annulynes reacted with potassium metal to form radical anions and dianions. The NMR chemical shifts of two internal protons of the dianion were negative and attributed to an aromatic diamagnetic ring current. The external proton next to the alkyne group had a chemical shift of nearly 14 and attributed to the positive charge of the potassium cation coordinated to it. Two new [12]annulyne isomers were reported in 2008 by the same groupThe Stevenson findings were challenged by Christl and Hopf in 2009. They were unable to conceive a plausible mechanism and argued that based on the available spectroscopic data the products formed were in fact two linear 1,3-hexadien-5-yne isomers and not macrocycles. Computational analysis of this compound suggests valence isomerization to biphenyl is very exothermic but also with a high kinetic barrier.[14]annulyne was reported in 1962 by Jackman et al.".
- Annulyne thumbnail Annulyne.png?width=300.
- Annulyne wikiPageID "3314447".
- Annulyne wikiPageLength "5447".
- Annulyne wikiPageOutDegree "28".
- Annulyne wikiPageRevisionID "584278454".
- Annulyne wikiPageWikiLink Alkene.
- Annulyne wikiPageWikiLink Alkyne.
- Annulyne wikiPageWikiLink Angle_strain.
- Annulyne wikiPageWikiLink Annulene.
- Annulyne wikiPageWikiLink Aromatic.
- Annulyne wikiPageWikiLink Aromatic_ring_current.
- Annulyne wikiPageWikiLink Aromaticity.
- Annulyne wikiPageWikiLink Aryne.
- Annulyne wikiPageWikiLink Benzyne.
- Annulyne wikiPageWikiLink Biphenyl.
- Annulyne wikiPageWikiLink Category:Alkynes.
- Annulyne wikiPageWikiLink Category:Annulenes.
- Annulyne wikiPageWikiLink Chemical_shift.
- Annulyne wikiPageWikiLink Cis–trans_isomerism.
- Annulyne wikiPageWikiLink Conjugated_system.
- Annulyne wikiPageWikiLink Diamagnetic_ring_current.
- Annulyne wikiPageWikiLink Electron_paramagnetic_resonance.
- Annulyne wikiPageWikiLink Electron_spin_resonance.
- Annulyne wikiPageWikiLink Franz_Sondheimer.
- Annulyne wikiPageWikiLink Hydrocarbon.
- Annulyne wikiPageWikiLink Isomer.
- Annulyne wikiPageWikiLink NMR_spectroscopy.
- Annulyne wikiPageWikiLink Nuclear_magnetic_resonance_spectroscopy.
- Annulyne wikiPageWikiLink Organic_chemistry.
- Annulyne wikiPageWikiLink Potassium_tert-butoxide.
- Annulyne wikiPageWikiLink Radical_ion.
- Annulyne wikiPageWikiLink Reactive_intermediate.
- Annulyne wikiPageWikiLink Ring_strain.
- Annulyne wikiPageWikiLink Room_temperature.
- Annulyne wikiPageWikiLink Trans_isomer.
- Annulyne wikiPageWikiLink Valence_isomerization.
- Annulyne wikiPageWikiLink File:-12-annulene.png.
- Annulyne wikiPageWikiLink File:Annulyne.png.
- Annulyne wikiPageWikiLink File:Annulynetrimerization.png.
- Annulyne wikiPageWikiLinkText "Annulyne".
- Annulyne wikiPageWikiLinkText "annulyne".
- Annulyne hasPhotoCollection Annulyne.
- Annulyne wikiPageUsesTemplate Template:Reflist.
- Annulyne subject Category:Alkynes.
- Annulyne subject Category:Annulenes.
- Annulyne hypernym Hydrocarbons.
- Annulyne type ChemicalCompound.
- Annulyne type Alkyne.
- Annulyne type Cycloalkene.
- Annulyne type Hydrocarbon.
- Annulyne comment "Annulynes or 1,2-didehydroannulenes are conjugated monocyclic hydrocarbons with alternating alkene bonds in addition to at least one alkyne bond. They are related to annulenes who have just alternating double bonds. The smallest member of this class is [4]annulyne but is never observed because the molecule carries too much angle strain. The next member is [6]annulyne or benzyne which is a reactive intermediate well known in organic chemistry.".
- Annulyne label "Annulyne".
- Annulyne sameAs Annulyne.
- Annulyne sameAs m.0955bm.
- Annulyne sameAs Q2851803.
- Annulyne sameAs Q2851803.
- Annulyne wasDerivedFrom Annulyne?oldid=584278454.
- Annulyne depiction Annulyne.png.
- Annulyne isPrimaryTopicOf Annulyne.