Hypercubane

{{chembox | ImageFile1 = Hypercubane.svg | ImageFile2 = Hypercubane-3D-bs-17.png | IUPACName = heptadecacyclo[5.5.5.5^10,17.5^15,15.3^7,16.0^4,14.0^14,17.2^1,27.2^4,30.2^20,23.2^20,27.2^23,30.0^10,18.0^13,18.0^13,26.0^16,19.0^19,26]tetraconta-2,5,8,11,21,24,28,31,33,35,37,39-dodecaene |Section1={{Chembox Identifiers | CASNo = 1627580-03-3 | CASNo_Ref = {{cascite|correct|CAS}} | PubChem = 165360254 | SMILES=C/1=C/C\28/C=C\C\39\C=C/C\46/C=C\C17/C=C\C/5%15\C=C/C%13(/C=C2)\C=C/C%11(/C=C3)\C=C/C(/C=C4)(\C=C5)C%12%17C6%10C7%16C8%14C9%10C%11%12C%13%14C%15%16%17 | StdInChI=1S/C40H24/c1-2-26-7-9-29-15-11-27-5-3-25(1)4-6-28-12-16-30(10-8-26)20-23-32(22-19-29)24-21-31(17-13-27,18-14-28)39-35(27)33(25)34(26)37(29,35)40(32,39)38(30,34)36(28,33)39/h1-24H | StdInChIKey=FFMFUIDOGFAUOP-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=40 | H=24 }} }}

'''Hypercubane''' is a hypothetical polycyclic hydrocarbon with the chemical formula C₄₀H₂₄. It is a molecular analog of the four-dimensional hypercube or tesseract. Hypercubane possesses an unconventional geometry of the carbon framework. It has ''O_h'' symmetry like classic cubane C₈H₈. The structure is that of octamethyl cubane—a carbon attached to each corner of cubane itself—having each of those carbon substituents joined to each of its neighbors by an ethylene-1,2-diyl linker to form an outer cage. The edge of each inner core and its outer linker form a cyclohexene.

== History == Hypercubane was first proposed in 2014 by Pichierri and studied computationally by density functional theory.<ref name=pichierri2014>{{cite journal|title=Hypercubane: DFT-based prediction of an ''O_h''-symmetric double-shell hydrocarbon|first=Fabio|last=Pichierri|journal=Chemical Physics Letters|date=2014|volume=612|pages=198–202|doi=10.1016/j.cplett.2014.08.032|bibcode=2014CPL...612..198P}}</ref> The initial model of hypercubane was constructed from octamethylcubane by removing unnecessary hydrogen atoms and adding the ethylene bridges as well as intercarbon bonds between the sp² and sp³ atoms. To facilitate the future hypercubane spectroscopic identification chemical shifts for both ¹³C and ¹H NMR-active nuclei have been calculated by Pichierri.<ref name="pichierri2014"/> Two years later, in 2016, studying the pyrolysis of hypercubane by means of tight-binding molecular dynamics simulations, Maslov and Katin demonstrated that hypercubane possessed high thermal stability comparable with the classic cubane C₈H₈.<ref name=maslov2016>{{cite journal|title=High kinetic stability of hypercubane: Tight-binding molecular dynamics study|first1=Mikhail M.|last1=Maslov|first2=Konstantin P.|last2=Katin|journal=Chemical Physics Letters|date=2016|volume=644|pages=280–283|doi=10.1016/j.cplett.2015.12.022|bibcode=2016CPL...644..280M}}</ref> It was shown that hypercubane lifetime at room temperature tended to infinity. Therefore, it can be assumed that hypercubane is a kinetically stable molecular system. Among the possible hypercubane decomposition products at high temperatures (more than 1000 K) one can observe polycyclic airscrew-like hydrocarbon C₃₄H₁₈ based on three combined graphene fragments passivated by hydrogen atoms and three isolated acetylene molecules.<ref name="maslov2016"/>

== Synthesis == As of {{CURRENTYEAR}}, there has been no method describing the synthesis of hypercubane.

== See also == *Basic zinc acetate and basic beryllium acetate, which have a structure resembling a 5-cell

== References == {{reflist}} {{theoretical-chem-stub}}

Category:Hypothetical chemical compounds Category:Molecular geometry Category:Cubanes