Hemispiroalkaplanes: Hydrocarbon Cage Systems with a Pyramidal-Tetracoordinate Carbon Atom and Remarkable Basicity
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.author | Rasmussen, Danne | |
---|---|---|
dc.contributor.author | Radom, Leo | |
dc.date.accessioned | 2015-12-13T23:18:17Z | |
dc.date.available | 2015-12-13T23:18:17Z | |
dc.identifier.issn | 0947-6539 | |
dc.identifier.uri | http://hdl.handle.net/1885/90104 | |
dc.description.abstract | 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 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.publisher | Wiley-VCH Verlag GMBH | |
dc.source | Chemistry, A European Journal | |
dc.subject | Keywords: 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.title | Hemispiroalkaplanes: Hydrocarbon Cage Systems with a Pyramidal-Tetracoordinate Carbon Atom and Remarkable Basicity | |
dc.type | Journal article | |
local.description.notes | Imported from ARIES | |
local.description.refereed | Yes | |
local.identifier.citationvolume | 6 | |
dc.date.issued | 2000 | |
local.identifier.absfor | 030505 - Physical Organic Chemistry | |
local.identifier.ariespublication | MigratedxPub20382 | |
local.type.status | Published Version | |
local.contributor.affiliation | Rasmussen, Danne, College of Physical and Mathematical Sciences, ANU | |
local.contributor.affiliation | Radom, Leo, College of Physical and Mathematical Sciences, ANU | |
local.bibliographicCitation.startpage | 2470 | |
local.bibliographicCitation.lastpage | 2483 | |
dc.date.updated | 2015-12-12T08:56:15Z | |
local.identifier.scopusID | 2-s2.0-0034600793 | |
Collections | ANU Research Publications |
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