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Hemispiroalkaplanes: Hydrocarbon Cage Systems with a Pyramidal-Tetracoordinate Carbon Atom and Remarkable Basicity

Rasmussen, Danne; Radom, Leo

Description

A new class of saturated hydrocarbons, in which a spiropentane-type unit is bound by a cyclic hydrocarbon, has been investigated by using ab initio molecular orbital calculations at the B3-LYP and MP2 levels. These molecules have been given the trivial name hemispiroalkaplanes. Hemialkaplanes, which are analogous molecules built-up from a neopentane-type unit and a cyclic hydrocarbon, have also been examined. The hemispiroalkaplanes are predicted to contain a pyramidal-tetra-coordinate carbon...[Show more]

dc.contributor.authorRasmussen, Danne
dc.contributor.authorRadom, Leo
dc.date.accessioned2015-12-13T23:18:17Z
dc.date.available2015-12-13T23:18:17Z
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/1885/90104
dc.description.abstractA new class of saturated hydrocarbons, in which a spiropentane-type unit is bound by a cyclic hydrocarbon, has been investigated by using ab initio molecular orbital calculations at the B3-LYP and MP2 levels. These molecules have been given the trivial name hemispiroalkaplanes. Hemialkaplanes, which are analogous molecules built-up from a neopentane-type unit and a cyclic hydrocarbon, have also been examined. The hemispiroalkaplanes are predicted to contain a pyramidal-tetra-coordinate carbon atom that possesses a lone pair of electrons. Protonation at this apical carbon atom is found to be highly favourable, resulting in a remarkably high basicity for a saturated hydrocarbon. The proton affinities of the hemispiroalkaplanes are calculated to be more than 1170 kJ mol-1, even greater than that of the diamine "proton sponges". Structural parameters, heats of formation and strain energies for the novel hydrocarbons are detailed.
dc.publisherWiley-VCH Verlag GMBH
dc.sourceChemistry, A European Journal
dc.subjectKeywords: carbon; hydrocarbon; spiro compound; alkalinity; article; calculation; chemical analysis; chemical structure; geometry; proton transport; thermodynamics Ab initio calculations; Basicity; Cage compounds; Hydrocarbons; Pyramidal-tetracoordinate carbon
dc.titleHemispiroalkaplanes: Hydrocarbon Cage Systems with a Pyramidal-Tetracoordinate Carbon Atom and Remarkable Basicity
dc.typeJournal article
local.description.notesImported from ARIES
local.description.refereedYes
local.identifier.citationvolume6
dc.date.issued2000
local.identifier.absfor030505 - Physical Organic Chemistry
local.identifier.ariespublicationMigratedxPub20382
local.type.statusPublished Version
local.contributor.affiliationRasmussen, Danne, College of Physical and Mathematical Sciences, ANU
local.contributor.affiliationRadom, Leo, College of Physical and Mathematical Sciences, ANU
local.bibliographicCitation.startpage2470
local.bibliographicCitation.lastpage2483
dc.date.updated2015-12-12T08:56:15Z
local.identifier.scopusID2-s2.0-0034600793
CollectionsANU Research Publications

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