Dimethanospiro(2.2)octaplane
{{correct title|reason=bracket|Dimethanospiro[2.2]octaplane}}
{{Chembox
|Name=Dimethanospiro[2.2]octaplane
|IUPACName= Dodecacyclo[11.10.0.01,5.02,13.02,21.03,18.06,15.08,23.09,14.011,20.012,14.012,17]tricosane
|ImageFile=Dimethanospiro(2.2)octaplane.png
|Section1={{Chembox Identifiers
|PubChem=100967056
| 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
| InChIKey = LMDPKFRIIOUORN-UHFFFAOYSA-N
| SMILES = C1C2C3CC4C5CC6C7C48C39C83C48C2CC5C34C6CC8C1C9C7
}}
|Section2={{Chembox Properties
| C=23 | H=24
}}
}}
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 rather than the usual tetrahedral geometry of a carbon atom with four bonds.
Molecular architecture
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.{{cite journal |last1=Lyons |first1=Jennifer E. |last2=Rasmussen |first2=Danne R. |last3=McGrath |first3=Mark P. |last4=Nobes |first4=Ross H. |last5=Radom |first5=Leo |title=Octaplane: A Saturated Hydrocarbon with a Remarkably Low Ionization Energy Leading to a Cation with a Planar Tetracoordinate Carbon Atom |journal=Angewandte Chemie International Edition in English |date=2 September 1994 |volume=33 |issue=1516 |pages=1667–1668 |doi=10.1002/anie.199416671}} The parent structure octaplane itself is expected to have a very low ionization potential and a square–planar geometry as the monocation, however calculations on the neutral compound found that the central carbon would distort to a square–pyramidal geometry.
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.{{cite book |last1=Dodziuk |first1=Helena |title=Strained Hydrocarbons: Beyond the van't Hoff and Le Bel Hypothesis |date=2009 |publisher=John Wiley & Sons |isbn=9783527627141 |page=48 |url=https://books.google.com/books?id=rpPULNO9XN4C&pg=PA48 |language=en}}{{cite book |last1=Lewars |first1=Errol G. |title=Modeling Marvels: Computational Anticipation of Novel Molecules |url=https://archive.org/details/modelingmarvelsc00lewa_400 |url-access=limited |date=2008 |publisher=Springer Netherlands |isbn=9781402069734 |pages=[https://archive.org/details/modelingmarvelsc00lewa_400/page/n11 1]–12 |language=en |chapter=Planar Carbon|doi=10.1007/978-1-4020-6973-4_1 }}{{cite journal |last1=Yang |first1=Li-Ming |last2=Ganz |first2=Eric |last3=Chen |first3=Zhongfang |last4=Wang |first4=Zhi-Xiang |last5=Schleyer |first5=Paul von Ragué |title=Four Decades of the Chemistry of Planar Hypercoordinate Compounds |url=https://apps.dtic.mil/dtic/tr/fulltext/u2/1009752.pdf |archive-url=https://web.archive.org/web/20190603133628/https://apps.dtic.mil/dtic/tr/fulltext/u2/1009752.pdf |url-status=live |archive-date=June 3, 2019 |journal=Angewandte Chemie International Edition |volume=54 |issue=33 |publisher=U.S. Army Research Office |pages=9468–9501 |doi=10.1002/anie.201410407 |pmid=26119555 |date=10 August 2015}}
References
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Category:Hypothetical chemical compounds
Category:Polycyclic nonaromatic hydrocarbons
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