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IUPAC name
3D model (JSmol)
  • InChI=1S/C23H24/c1-7-11-3-15-9-2-10-17-5-13-8(1)14-6-18(10)22-16(9)4-12(7)20(14,22)23(22)19(11,13)21(15,17)23/h7-18H,1-6H2
  • C1C2C3CC4C5CC6C7C48C39C83C48C2CC5C34C6CC8C1C9C7
Molar mass 300.445 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dimethanospiro[2.2]octaplane is a hypothetical saturated hydrocarbon that is expected to have a carbon atom in with a stable, unusual square-planar coordination[1] rather than the usual tetrahedral geometry of a carbon atom with four bonds.

Molecular architecture[edit]

An octaplane contains a central carbon atom is surrounded by four carbon atoms, which are held in place by perpendicular links to two cyclooctane rings above and below.[2] The parent structure octaplane itself is expected to have a very low ionization potential and a square–planar geometry as the monocation,[2] however calculations on the neutral compound found that the central carbon would distort to a square–pyramidal geometry.[1]

In dimethanospiro[2.2]octaplane, two pairs of the carbons attached to the central one are bonded to each other to make a spiropentane, and there are two methylene linkages between the two cyclooctane rings.[1][3][4]


  1. ^ a b c Dodziuk, Helena (2009). Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis. John Wiley & Sons. p. 48. ISBN 9783527627141.
  2. ^ a b Lyons, Jennifer E.; Rasmussen, Danne R.; McGrath, Mark P.; Nobes, Ross H.; Radom, Leo (2 September 1994). "Octaplane: A Saturated Hydrocarbon with a Remarkably Low Ionization Energy Leading to a Cation with a Planar Tetracoordinate Carbon Atom". Angewandte Chemie International Edition in English. 33 (1516): 1667–1668. doi:10.1002/anie.199416671.
  3. ^ Lewars, Errol G. (2008). "Planar Carbon". Modeling Marvels: Computational Anticipation of Novel Molecules. Springer Netherlands. pp. 1–12. doi:10.1007/978-1-4020-6973-4_1. ISBN 9781402069734.
  4. ^ Yang, Li-Ming; Ganz, Eric; Chen, Zhongfang; Wang, Zhi-Xiang; Schleyer, Paul von Ragué (10 August 2015). "Four Decades of the Chemistry of Planar Hypercoordinate Compounds" (PDF). Angewandte Chemie International Edition. U.S. Army Research Office. 54 (33): 9468–9501. doi:10.1002/anie.201410407. PMID 26119555. Archived (PDF) from the original on June 3, 2019.