Octanitrocubane

{{chembox

| Watchedfields = changed

| verifiedrevid = 427724099

| ImageFileL1 = Octanitrocubane.svg

| ImageFileR1 = Octanitrocubane-3D-balls.png

| ImageClassL1 = skin-invert

| PIN = Octanitrocubane

| OtherNames =

|Section1 = {{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9937054

| InChI = 1/C8N8O16/c17-9(18)1-2(10(19)20)5(13(25)26)3(1,11(21)22)7(15(29)30)4(1,12(23)24)6(2,14(27)28)8(5,7)16(31)32

| InChIKey = URIPDZQYLPQBMG-UHFFFAOYAW

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C8N8O16/c17-9(18)1-2(10(19)20)5(13(25)26)3(1,11(21)22)7(15(29)30)4(1,12(23)24)6(2,14(27)28)8(5,7)16(31)32

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = URIPDZQYLPQBMG-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 99393-63-2

| PubChem = 11762357

| SMILES = [O-][N+](=O)C12C3([N+]([O-])=O)C4([N+]([O-])=O)C1([N+]([O-])=O)C5([N+]([O-])=O)C2([N+]([O-])=O)C3([N+]([O-])=O)C45[N+]([O-])=O

}}

|Section2 = {{Chembox Properties

| C=8|N=8|O=16

| Appearance = White solid

| Density = 1.979 g/cm³

| MeltingPtC = 200

| MeltingPt_notes= (sublimes)

| BoilingPt =

| Solubility =

| SolubleOther = Slightly soluble in hexane, soluble in ethanol

}}

|Section3 = {{Chembox Hazards

| MainHazards = Explosive compound

| FlashPt =

| AutoignitionPt =

}}

|Section6 = {{Chembox Explosive

| ShockSens = Low

| FrictionSens = Low

| DetonationV = 10,100{{nbsp}}m/s

}}

|Section8 = {{Chembox Related

| OtherCompounds = Cubane
Heptanitrocubane
Octafluorocubane

}}

}}

Octanitrocubane (molecular formula: C₈(NO₂)₈) is a proposed high explosive that, like TNT, is shock-insensitive (not readily detonated by shock).{{cite web|url=http://www-news.uchicago.edu/releases/01/010320.explosive.shtml|title=Octanitrocubane: Easier said than done|publisher=University of Chicago News Office|date=March 20, 2001}} The octanitrocubane molecule has the same chemical structure as cubane (C₈H₈) except that each of the eight hydrogen atoms is replaced by a nitro group (NO₂). As of 1998, octanitrocubane had not been produced in quantities large enough to test its performance as an explosive.

{{cite journal

| last1= Astakhov |first1=A. M.|last2= Stepanov |first2=R. S. |last3=Babushkin |first3=A. Yu.

| title = On the detonation parameters of octanitrocubane

| journal = Combustion, Explosion, and Shock Waves

| year = 1998

| volume = 34

| issue = 1

| pages= 85–87

| doi = 10.1007/BF02671823

|s2cid=98585631}}

It is, however, not as powerful an explosive as once thought, as the high-density theoretical crystal structure has not been achieved. For this reason, heptanitrocubane, the slightly less nitrated form, is believed to have marginally better performance, despite having a worse oxygen balance.

Octanitrocubane is thought to have 20–25% greater performance than HMX (octogen). This increase in power is due to its highly expansive breakdown into CO₂ and N₂, as well as to the presence of strained chemical bonds in the molecule which have stored potential energy. In addition, it produces no water vapor upon combustion, making it less visible, and both the chemical itself and its decomposition products (nitrogen and carbon dioxide) are considered to be non-toxic.

Octanitrocubane was first synthesized by Philip Eaton (who was also the first to synthesize cubane in 1964) and Mao-Xi Zhang at the University of Chicago in 1999, with the structure proven by crystallographer Richard Gilardi of the United States Naval Research Laboratory.

{{cite journal

| first1= Mao-Xi|last1= Zhang|first2= Philip E.|last2= Eaton|first3= Richard |last3=Gilardi

| title = Hepta- and Octanitrocubanes

| journal = Angewandte Chemie International Edition

| year = 2000

| volume = 39

| issue = 2

| pages= 401–404

| doi = 10.1002/(SICI)1521-3773(20000117)39:2<401::AID-ANIE401>3.0.CO;2-P

| pmid=10649425

}}

{{cite journal

| first1= Philip E.|last1= Eaton|first2= Mao-Xi|last2= Zhang|first3= Richard|last3= Gilardi|first4= Nat|last4= Gelber|first5= Sury|last5= Iyer|first6= Rao |last6=Surapaneni

| title = Octanitrocubane: A New Nitrocarbon

| journal = Propellants, Explosives, Pyrotechnics

| year = 2001

| volume = 27

| issue = 1

| pages= 1–6

| doi = 10.1002/1521-4087(200203)27:1<1::AID-PREP1>3.0.CO;2-6

}}