| Revision as of 20:33, 3 December 2010 editGinogrz (talk | contribs)153 editsNo edit summary← Previous edit |
Latest revision as of 17:21, 8 September 2024 edit undoCitation bot (talk | contribs)Bots5,459,086 edits Added bibcode. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Benzene derivatives | #UCB_Category 11/29 |
| (42 intermediate revisions by 21 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
|Watchedfields = changed |
|
| verifiedrevid = 400109853 |
|
|verifiedrevid = 400368712 |
| ⚫ |
|ImageFile=Hexaphenylbenzene.png |
|
|
|
|ImageFile = Structural formula of hexaphenylbenzene.svg |
|
|ImageSize= |
|
|
|
|ImageFile2 =Hexaphenylbenzene_xtal.png |
|
|IUPACName=1,2,3,4,5,6-hexa(phenyl)benzene |
|
|
|
|PIN = 2<sup>3</sup>,2<sup>4</sup>,2<sup>5</sup>,2<sup>6</sup>-Tetraphenyl-1<sup>1</sup>,2<sup>1</sup>:2<sup>2</sup>,3<sup>1</sup>-terphenyl |
|
|OtherNames= |
|
|
⚫ |
|OtherNames = Hexaphenylbenzene |
|
|Section1={{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
| InChI = 1/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H |
|
|InChI = 1/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H |
|
| InChIKey = QBHWPVJPWQGYDS-UHFFFAOYAG |
|
|InChIKey = QBHWPVJPWQGYDS-UHFFFAOYAG |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChI = 1S/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H |
|
|StdInChI = 1S/C42H30/c1-7-19-31(20-8-1)37-38(32-21-9-2-10-22-32)40(34-25-13-4-14-26-34)42(36-29-17-6-18-30-36)41(35-27-15-5-16-28-35)39(37)33-23-11-3-12-24-33/h1-30H |
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| StdInChIKey = QBHWPVJPWQGYDS-UHFFFAOYSA-N |
|
|StdInChIKey = QBHWPVJPWQGYDS-UHFFFAOYSA-N |
|
|
|CASNo_Ref = {{cascite|correct|??}} |
|
| CASNo=992-04-1 |
|
|CASNo =992-04-1 |
|
| PubChem=70432 |
|
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
| UNII = 35L5JAJ94N |
| ⚫ |
| ChemSpiderID = 63611 |
|
|
|
|PubChem =70432 |
| ⚫ |
| SMILES = c1cc(ccc1)c3c(c(c(c(c3c2ccccc2)c4ccccc4)c5ccccc5)c6ccccc6)c7ccccc7 |
|
|
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
⚫ |
|ChemSpiderID = 63611 |
|
⚫ |
|SMILES = c1cc(ccc1)c3c(c(c(c(c3c2ccccc2)c4ccccc4)c5ccccc5)c6ccccc6)c7ccccc7 |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
|
|C=42|H=30 |
|
| Formula=C<sub>42</sub>H<sub>30</sub> |
|
|
⚫ |
|Appearance = white solid |
|
| MolarMass=534.6876 |
|
|
|
|MeltingPtC = 454 to 456 |
| ⚫ |
| Appearance= |
|
|
⚫ |
|MeltingPt_ref = <ref name = fieser/> |
|
| Density= |
|
| ⚫ |
| MeltingPt=454-456 °C<ref name = fieser/> |
|
|
| BoilingPt= |
|
|
| Solubility= |
|
| ⚫ |
}} |
|
|
|Section3={{Chembox Hazards |
|
|
| MainHazards= |
|
|
| FlashPt= |
|
|
| Autoignition= |
|
|
}} |
|
|
}} |
|
}} |
|
⚫ |
}} |
|
'''Hexaphenylbenzene''' is an ] composed of a ] ring substituted with six ] rings. |
|
|
|
'''Hexaphenylbenzene''' is an ] composed of a ] ring substituted with six ] rings. It is a colorless solid. The compound is the parent member of a wider class of '''hexaarylbenzenes''', which are mainly of theoretical interest.<ref name="hexaarylbenzene review">{{cite journal|title=Hexaarylbenzene: Evolution of Properties and Applications of Multitalented Scaffold|author=Varun Vij, Vandana Bhalla, and Manoj Kumar|journal=Chemical Reviews|year=2016|volume=116|issue=16|pages=9565–9627|doi=10.1021/acs.chemrev.6b00144|pmid=27498592}}</ref> |
|
|
|
|
|
|
==Preparation== |
|
It may be prepared through a ] by refluxing ] and ] in ] or other high-temperature solvent.<ref name = fieser>{{OrgSynth | title = Hexaphenylbenzene | author = Louis Fieser | collvol = 5 | collvolpages = 604 | prep=cv5p0604 | year = 1973}}</ref> |
|
It is prepared by heating ] and ] in ] or other high-temperature solvent. The reaction proceeds via a ] to give the hexaphenyldienone, which then eliminates carbon monoxide.<ref name = fieser>{{cite journal| title = Hexaphenylbenzene | journal = Organic Syntheses | author = Louis Fieser | volume= 46 | pages = 44| year = 1966|doi=10.15227/orgsyn.046.0044}}</ref> |
|
|
|
|
|
:] |
|
:] |
|
|
|
|
|
|
Together with 1,2,3,4-tetraphenylnaphthalene, hexaphenylbenzene forms by the chromium-catalyzed oligomerization of ].<ref>{{cite journal|title=π-Complexes of the Transition Metals. X. Acetylenic π-Complexes of Chromium in Organic Synthesis|author=W. Herwig, W. Metlesics, H. Zeiss|journal=J. Am. Chem. Soc.|year=1959|volume=81|issue=23|pages=6203–6207|doi=10.1021/ja01532a024}}</ref> It may also be prepared by the ]-catalyzed ] of diphenylacetylene.<ref name="hexaarylbenzene review"/> |
| ⚫ |
Due to ] congestion among the phenyl rings, the stable ] of this molecule has these rings rotated out of the plane of the central benzene ring. In the crystalline form, molecule forms a propeller-like conformation in which the phenyl rings are rotated about 65°, while in the gas phase, they are perpendicular with some slight oscillations.<ref>{{cite journal |title= Restricted Rotation in Hexaarylbenzenes |author= Gust, D. |journal= ] |year= 1977 |volume= 99 |issue= 21 |pages= 6980–6982 |doi= 10.1021/ja00463a034 }}</ref> |
|
|
|
:] |
|
|
|
|
|
==Structure== |
|
|
] |
|
⚫ |
The stable ] of this molecule has the phenyl rings rotated out of the plane of the central benzene ring. The molecule adopts a propeller-like conformation in which the phenyl rings are rotated about 65°,<ref name = bart>{{cite journal | doi = 10.1107/S0567740868004176 | title = The crystal structure of a modification of hexaphenylbenzene | year = 1968 | last1 = Bart | first1 = J. C. J. | journal = Acta Crystallographica Section B | volume = 24 | issue = 10 | pages = 1277–1287 | bibcode = 1968AcCrB..24.1277B | url = http://journals.iucr.org/b/issues/1968/10/00/a06258/a06258.pdf }}{{Dead link|date=February 2022 |bot=InternetArchiveBot |fix-attempted=yes }}</ref> while in the gas phase, they are perpendicular with some slight oscillations.<ref>{{cite journal |title= Restricted Rotation in Hexaarylbenzenes |author= Gust, D. |journal= ] |year= 1977 |volume= 99 |issue= 21 |pages= 6980–6982 |doi= 10.1021/ja00463a034}}</ref> |
|
|
|
|
|
{{clear|left}} |
|
|
|
|
|
==References== |
|
==References== |
|
<References/> |
|
<References/> |
|
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
] |
|
|
|
|
] |
|
|
] |
|
|
] |
|