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- Fenestrane abstract "A fenestrane in organic chemistry is a type of chemical compound with a central quaternary carbon atom which serves as a common vertex for four fused carbocycles. They can be regarded as spiro compounds twice over. Because of their inherent strain and instability, fenestranes are of theoretical interest to chemists. The name—proposed in 1972 by Vlasios Georgian and Martin Saltzman—is derived from the Latin word for window: Fenestra.The smallest member of the family, consisting of 4 fused cyclopropane rings is [3.3.3.3]fenestrane or pyramidane—a molecule with an extensive history on its own. In the next member, 4 cyclobutane rings are fused, forming the archetypical window motif. It is called in its own chemical nomenclature [4.4.4.4]fenestrane simply by counting the number of carbon atoms in each ring. The formal name for this compound is tetracyclo[3.3.1.03,9.07,9]nonane.In an extreme case the central carbon atom ordinarily with a tetrahedral molecular geometry gets completely flattened. In the molecular orbital picture for square planar methane two of a total of 3 sp2 hybridized carbon atomic orbitals form regular bonds with two of the hydrogen atoms as in a planar alkene. The third sp2 orbital interacts in a three-center two-electron bond with the two remaining hydrogen atoms utilizing only the hydrogen electrons. Two additional carbon valence electrons are situated in a p-orbital perpendicular to the plane of the molecule. The four C-H bonds are equal because they resonate. In silico calculations show that it takes 95 to 250 kcal/mol (400 to 1,050 kJ/mol) for this process.One of the highest strained fenestranes actually isolated is a [4.4.4.5]fenestrane with bond angles through the central carbon atom of around 130° based on X-ray diffraction. In this molecule the bonds extending from the central carbon atom are shortened with bond lengths of 149 picometer while those at the perimeter are extended to 159 pm. (The C-C bond in ethane is 155 pm long.)The first ever synthesized fenestrane is a [4.5.5.6]fenestrane:".
- Fenestrane thumbnail Fenestranes.png?width=300.
- Fenestrane wikiPageID "6888823".
- Fenestrane wikiPageLength "6625".
- Fenestrane wikiPageOutDegree "65".
- Fenestrane wikiPageRevisionID "668555458".
- Fenestrane wikiPageWikiLink Acetal.
- Fenestrane wikiPageWikiLink Alicyclic_compound.
- Fenestrane wikiPageWikiLink Alkene.
- Fenestrane wikiPageWikiLink Aza-.
- Fenestrane wikiPageWikiLink Bicyclic_molecule.
- Fenestrane wikiPageWikiLink Bond_length.
- Fenestrane wikiPageWikiLink Borane.
- Fenestrane wikiPageWikiLink Carbon–carbon_bond.
- Fenestrane wikiPageWikiLink Cascade_reaction.
- Fenestrane wikiPageWikiLink Category:Alkanes.
- Fenestrane wikiPageWikiLink Category:Hydrocarbons.
- Fenestrane wikiPageWikiLink Chemical_compound.
- Fenestrane wikiPageWikiLink Chemical_nomenclature.
- Fenestrane wikiPageWikiLink Conrotatory_and_disrotatory.
- Fenestrane wikiPageWikiLink Copper(I)_cyanide.
- Fenestrane wikiPageWikiLink Cycloaddition.
- Fenestrane wikiPageWikiLink Cyclobutane.
- Fenestrane wikiPageWikiLink Cyclopropane.
- Fenestrane wikiPageWikiLink Diol.
- Fenestrane wikiPageWikiLink Electrocyclic_reaction.
- Fenestrane wikiPageWikiLink Enol_ether.
- Fenestrane wikiPageWikiLink Ethane.
- Fenestrane wikiPageWikiLink Haloalkane.
- Fenestrane wikiPageWikiLink Hydrogen_peroxide.
- Fenestrane wikiPageWikiLink Hydrogenation.
- Fenestrane wikiPageWikiLink In_silico.
- Fenestrane wikiPageWikiLink Latin.
- Fenestrane wikiPageWikiLink Methane.
- Fenestrane wikiPageWikiLink Mitsunobu_reaction.
- Fenestrane wikiPageWikiLink Molecular_geometry.
- Fenestrane wikiPageWikiLink Molecular_orbital.
- Fenestrane wikiPageWikiLink Nitronate.
- Fenestrane wikiPageWikiLink Nitroso.
- Fenestrane wikiPageWikiLink Nucleophilic_addition.
- Fenestrane wikiPageWikiLink Orbital_hybridisation.
- Fenestrane wikiPageWikiLink Organic_chemistry.
- Fenestrane wikiPageWikiLink Organocopper_compound.
- Fenestrane wikiPageWikiLink Organozinc_compound.
- Fenestrane wikiPageWikiLink Phenylselenenyl_bromide.
- Fenestrane wikiPageWikiLink Picometre.
- Fenestrane wikiPageWikiLink Potassium_carbonate.
- Fenestrane wikiPageWikiLink Raney_nickel.
- Fenestrane wikiPageWikiLink Redox.
- Fenestrane wikiPageWikiLink Resonance_(chemistry).
- Fenestrane wikiPageWikiLink Spiro_compound.
- Fenestrane wikiPageWikiLink Spiropentadiene.
- Fenestrane wikiPageWikiLink Square_planar_molecular_geometry.
- Fenestrane wikiPageWikiLink Strain_energy.
- Fenestrane wikiPageWikiLink Syn_and_anti_addition.
- Fenestrane wikiPageWikiLink Tetrahedral_molecular_geometry.
- Fenestrane wikiPageWikiLink Tetrahedrane.
- Fenestrane wikiPageWikiLink Three-center_two-electron_bond.
- Fenestrane wikiPageWikiLink Transmetalation.
- Fenestrane wikiPageWikiLink Trimethylaluminium.
- Fenestrane wikiPageWikiLink Valence_electron.
- Fenestrane wikiPageWikiLink Window.
- Fenestrane wikiPageWikiLink X-ray_crystallography.
- Fenestrane wikiPageWikiLink File:AzaFenestraneSynthesis.png.
- Fenestrane wikiPageWikiLink File:FenestraneHulot2008.svg.
- Fenestrane wikiPageWikiLink File:Fenestranes.png.
- Fenestrane wikiPageWikiLink File:FenstraneSynthesis1972.png.
- Fenestrane wikiPageWikiLinkText "Fenestrane".
- Fenestrane wikiPageWikiLinkText "fenestrane".
- Fenestrane wikiPageUsesTemplate Template:Citation_needed.
- Fenestrane wikiPageUsesTemplate Template:Reflist.
- Fenestrane subject Category:Alkanes.
- Fenestrane subject Category:Hydrocarbons.
- Fenestrane hypernym Compound.
- Fenestrane type ChemicalCompound.
- Fenestrane type Hydride.
- Fenestrane type Hydrocarbon.
- Fenestrane comment "A fenestrane in organic chemistry is a type of chemical compound with a central quaternary carbon atom which serves as a common vertex for four fused carbocycles. They can be regarded as spiro compounds twice over. Because of their inherent strain and instability, fenestranes are of theoretical interest to chemists.".
- Fenestrane label "Fenestrane".
- Fenestrane sameAs Q865893.
- Fenestrane sameAs Fenestraan.
- Fenestrane sameAs Fenestrano.
- Fenestrane sameAs m.0gvfg5.
- Fenestrane sameAs Фенестрани.
- Fenestrane sameAs Q865893.
- Fenestrane sameAs 窗烷.
- Fenestrane wasDerivedFrom Fenestrane?oldid=668555458.
- Fenestrane depiction Fenestranes.png.
- Fenestrane isPrimaryTopicOf Fenestrane.