Display options
Cite
Rasmussen DR, Radom L. Hemispiroalkaplanes: hydrocarbon cage systems with a pyramidal-tetracoordinate carbon atom and remarkable basicity. Chemistry. 2000;6(13):2470-83doi: 10.1002/1521-3765(20000703)6:13<2470::aid-chem2470>3.0.co;2-k.
Rasmussen, D. R., & Radom, L. (2000). Hemispiroalkaplanes: hydrocarbon cage systems with a pyramidal-tetracoordinate carbon atom and remarkable basicity. Chemistry (Weinheim an der Bergstrasse, Germany), 6(13), 2470-83. https://doi.org/10.1002/1521-3765(20000703)6:13<2470::aid-chem2470>3.0.co;2-k
Rasmussen, and Radom. "Hemispiroalkaplanes: hydrocarbon cage systems with a pyramidal-tetracoordinate carbon atom and remarkable basicity." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 6,13 (2000): 2470-83. doi: https://doi.org/10.1002/1521-3765(20000703)6:13<2470::aid-chem2470>3.0.co;2-k
Rasmussen DR, Radom L. Hemispiroalkaplanes: hydrocarbon cage systems with a pyramidal-tetracoordinate carbon atom and remarkable basicity. Chemistry. 2000 Jul 03;6(13):2470-83. doi: 10.1002/1521-3765(20000703)6:13<2470::aid-chem2470>3.0.co;2-k. PMID: 10939749.
Copy Download .nbib Format: NLM
Share it on

Chemistry. 2000 Jul 03;6(13):2470-83. doi: 10.1002/1521-3765(20000703)6:13<2470::aid-chem2470>3.0.co;2-k.

Hemispiroalkaplanes: hydrocarbon cage systems with a pyramidal-tetracoordinate carbon atom and remarkable basicity.

Chemistry (Weinheim an der Bergstrasse, Germany)

Rasmussen, Radom

Affiliations

  1. Research School of Chemistry, Australian National University, Canberra, ACT.

PMID: 10939749 DOI: 10.1002/1521-3765(20000703)6:13<2470::aid-chem2470>3.0.co;2-k

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-tetracoordinate 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 kJmol(-1), even greater than that of the diamine "proton sponges". Structural parameters, heats of formation and strain energies for the novel hydrocarbons are detailed.

Publication Types