| Revision as of 22:14, 19 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[WP:CHEMVALID|Chem/Drugbox validation← Previous edit |
Latest revision as of 13:02, 1 May 2024 edit undoAlfa-ketosav (talk | contribs)Extended confirmed users2,258 edits →References |
| (15 intermediate revisions by 14 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
| ⚫ |
| verifiedrevid = 435704948 |
|
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 451403232 |
|
| ImageFile = Sumanene.svg |
|
| ImageFile = Sumanene.svg |
|
| ImageSize = 156px |
|
| ImageSize = 156px |
|
| ImageFile1 = Sumanene3D.png |
|
| ImageFile1 = Sumanene3D.png |
|
| ImageSize1 = 180px |
|
| ImageSize1 = 180px |
|
| IUPACName = 4,7-Dihydro-1H-tricyclopentatriphenylene |
|
| PIN = 4,7-Dihydro-1''H''-tricyclopentatriphenylene |
|
| OtherNames = |
|
| OtherNames = |
|
| Section1 = {{Chembox Identifiers |
|
|Section1={{Chembox Identifiers |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
| CASNo = 151253-59-7 |
|
| CASNo = 151253-59-7 |
| ⚫ |
| PubChem = |
|
|
|
| UNII_Ref = {{fdacite|correct|FDA}} |
| ⚫ |
| SMILES = C16=C5C4=C3C2=C1C7=CC=C2 CC3=CC=C4CC5=CC=C6C7 |
|
|
|
| UNII = TX2KR8MQM9 |
| ⚫ |
}} |
|
|
⚫ |
| SMILES = C16=C5C4=C3C2=C1C7=CC=C2CC3=CC=C4CC5=CC=C6C7 |
| ⚫ |
| Section2 = {{Chembox Properties |
|
|
⚫ |
| PubChem = 11173107 |
| ⚫ |
| C=21|H=12 |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
| ⚫ |
| MolarMass = 264.32 |
|
|
| Appearance = |
|
| ChemSpiderID = 9348199 |
|
|
| InChI = 1/C21H12/c1-2-11-8-13-5-6-15-9-14-4-3-12-7-10(1)16-17(11)19(13)21(15)20(14)18(12)16/h1-6H,7-9H2 |
| ⚫ |
| Density = |
|
|
|
| InChIKey = WOYKPMSXBVTRKZ-UHFFFAOYAE |
| ⚫ |
| MeltingPt = |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
| ⚫ |
| BoilingPt = |
|
|
|
| StdInChI = 1S/C21H12/c1-2-11-8-13-5-6-15-9-14-4-3-12-7-10(1)16-17(11)19(13)21(15)20(14)18(12)16/h1-6H,7-9H2 |
| ⚫ |
| Solubility = |
|
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
| ⚫ |
}} |
|
|
|
| StdInChIKey = WOYKPMSXBVTRKZ-UHFFFAOYSA-N |
| ⚫ |
| Section3 = {{Chembox Hazards |
|
|
⚫ |
}} |
| ⚫ |
| MainHazards = |
|
|
⚫ |
|Section2={{Chembox Properties |
| ⚫ |
| FlashPt = |
|
|
⚫ |
| C=21 | H=12 |
|
| Autoignition = |
|
|
⚫ |
| MolarMass = 264.32 |
| ⚫ |
}} |
|
|
|
| Appearance = |
|
⚫ |
| Density = |
|
⚫ |
| MeltingPt = |
|
⚫ |
| BoilingPt = |
|
⚫ |
| Solubility = |
|
⚫ |
}} |
|
⚫ |
|Section3={{Chembox Hazards |
|
⚫ |
| MainHazards = |
|
⚫ |
| FlashPt = |
|
|
| AutoignitionPt = |
|
⚫ |
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Sumanene''' is a ] and of scientific interest because the ] can be considered a fragment of ]. ''Suman'' means "]" in both ] and ].<ref>''Towards the design of tricyclopenta triphenylene (sumanene): a bowl-shaped hydrocarbon featuring a structural motif present in C<sub>60</sub> (buckminsterfullerene)'' Goverdhan Mehta, Shailesh R. Shah and K. Ravikumar Journal of the Chemical Society, ], '''1993''', (12), 1006 - 1008 {{DOI|10.1039/C39930001006}}</ref> The core of the ] is a ] ring and the ] consists of alternating benzene rings (3) and ] rings (3). Unlike ], sumanene has ] positions which are available for ]s. |
|
'''Sumanene''' is a ] and of scientific interest because the ] can be considered a fragment of ]. ''Suman'' means "]" in both ] and ].<ref>''Towards the design of tricyclopenta triphenylene (sumanene): a bowl-shaped hydrocarbon featuring a structural motif present in C<sub>60</sub> (buckminsterfullerene)'' ], Shailesh R. Shah and K. Ravikumar Journal of the Chemical Society, ], '''1993''', (12), 1006 - 1008 {{doi|10.1039/C39930001006}}</ref> The core of the ] is a ] ring and the ] consists of alternating benzene rings (3) and ] rings (3). Unlike ], sumanene has ] positions which are available for ]s. |
|
|
|
|
|
== Organic synthesis == |
|
== Organic synthesis == |
|
The structure of Sumanene can be inferred from ] of 1,5,9-trimethyl] but the first practical synthesis starts from ].<ref>''A Synthesis of Sumanene, a Fullerene Fragment'' Hidehiro Sakurai, Taro Daiko, and Toshikazu Hirao ], Vol 301, Issue 5641, 1878 , 26 September '''2003''' {{DOI|10.1126/science.1088290}}</ref> Norbornadiene is converted into a ] by action of ], ] and ]. A ] of this stannane with ] affords the benzene core. The ] groups created in this conversion then migrate in a ] ] and ] by the ]. The final structure is obtained by ] by ]. |
|
The structure of Sumanene can be inferred from ] of 1,5,9-trimethyl] but the first practical synthesis starts from ].<ref>''A Synthesis of Sumanene, a Fullerene Fragment'' Hidehiro Sakurai, Taro Daiko, and Toshikazu Hirao ], Vol 301, Issue 5641, 1878 , 26 September '''2003''' {{doi|10.1126/science.1088290}}</ref> Norbornadiene is converted into a ] by action of ], ] and ]. An ] of this stannane with ] affords the benzene core. The ] (-{{chem|CH|2}}-) created in this conversion then migrate in a ] ] and ] by the ]. The final structure is obtained by ] by ]. |
|
|
|
|
|
|
|
:] |
|
:] |
|
|
|
|
|
== Properties == |
|
== Properties == |
|
Sumanene is a ]-shaped ] with a bowl depth of 118 ]s.<ref>''Structural Elucidation of Sumanene and Generation of Its Benzylic Anions '' Hidehiro Sakurai, Taro Daiko, Hiroyuki Sakane, Toru Amaya, and Toshikazu Hirao ], 127 (33), 11580 -11581, '''2005''' {{DOI|10.1021/ja0518169}}</ref> The 6 hub carbon atoms are ] by 9° and the molecule displays considerable bond alternation (138.1 to 143.1 pm). Sumanene also experiences '''bowl-to-bowl inversion''' with an ] of 19.6 ]/] (82 ]/mol) at 140 °C which is much higher than that found for its ] cousin. |
|
Sumanene is a ]-shaped ] with a bowl depth of 118 ]s.<ref>''Structural Elucidation of Sumanene and Generation of Its Benzylic Anions '' Hidehiro Sakurai, Taro Daiko, Hiroyuki Sakane, Toru Amaya, and Toshikazu Hirao ], 127 (33), 11580 -11581, '''2005''' {{doi|10.1021/ja0518169}}</ref> The 6 hub carbon atoms are ] by 9° and the molecule displays considerable bond alternation (138.1 to 143.1 pm). Sumanene also experiences '''bowl-to-bowl inversion''' with an ] of 19.6 ]/] (82 ]/mol) at 140 °C which is much higher than that found for its ] cousin. |
|
Like any benzylic ], the sumanene protons can be abstracted by a strong ] such as ] to form the sumanene mono ]. This strong ] can react with an ] such as ] to the ] derivative. |
|
Like any benzylic ], the sumanene protons can be abstracted by a strong ] such as ] to form the sumanene mono ]. This strong ] can react with an ] such as ] to the ] derivative. |
|
|
|
|
|
The trianion has also been reported <ref>Hidehiro Sakurai, Taro Daiko, Hiroyuki Sakane, Toru Amaya, and Toshikazu Hira; J. Am. Chem. Soc., 2005, 127 (33), pp 11580–11581 {{DOI|10.1021/ja0518169}}</ref>. Electron transport properties have been investigated <ref>''Anisotropic Electron Transport Properties in Sumanene Crystal'' Toru Amaya, Shu Seki, Toshiyuki Moriuchi, Kana Nakamoto, Takuto Nakata, Hiroyuki Sakane, Akinori Saeki, Seiichi Tagawa and Toshikazu Hirao J. Am. Chem. Soc., 2009, 131 (2), pp 408–409 {{DOI|10.1021/ja805997v}}</ref> <ref>''The electrochemical inspection of the redox activity of sumanene and its concave CpFe complex'' Piero Zanello, Serena Fedi, Fabrizia Fabrizi de Biani, Gianluca Giorgi, Toru Amaya, Hiroyuki Sakane and Toshikazu Hirao |
|
The trianion has also been reported.<ref>Hidehiro Sakurai, Taro Daiko, Hiroyuki Sakane, Toru Amaya, and Toshikazu Hira; J. Am. Chem. Soc., 2005, 127 (33), pp 11580–11581 {{doi|10.1021/ja0518169}}</ref> Electron transport properties have been investigated <ref>''Anisotropic Electron Transport Properties in Sumanene Crystal'' Toru Amaya, Shu Seki, Toshiyuki Moriuchi, Kana Nakamoto, Takuto Nakata, Hiroyuki Sakane, Akinori Saeki, Seiichi Tagawa and Toshikazu Hirao J. Am. Chem. Soc., 2009, 131 (2), pp 408–409 {{doi|10.1021/ja805997v}}</ref><ref>''The electrochemical inspection of the redox activity of sumanene and its concave CpFe complex'' Piero Zanello, Serena Fedi, Fabrizia Fabrizi de Biani, Gianluca Giorgi, Toru Amaya, Hiroyuki Sakane and Toshikazu Hirao |
|
Dalton Trans., 2009, 9192-9197 {{DOI|10.1039/B910711H}} </ref> as well as ] <ref>''Solid-state 13C NMR investigations of 4,7-dihydro-1H-tricyclopentatriphenylene (sumanene) and indenofluoranthene: Buckminsterfullerene moieties'' Merrill D. Halling, Anita M. Orendt, Mark Strohmeier, Mark S. Solum, Vikki M. Tsefrikas, Toshikazu Hirao, Lawrence T. Scott, Ronald J. Pugmire and David M. Grant Phys. Chem. Chem. Phys., 2010, 12, 7934-7941 {{DOI|10.1039/C001903H}} </ref> |
|
Dalton Trans., 2009, 9192-9197 {{doi|10.1039/B910711H}}</ref> as well as ]<ref>''Solid-state 13C NMR investigations of 4,7-dihydro-1H-tricyclopentatriphenylene (sumanene) and indenofluoranthene: Buckminsterfullerene moieties'' Merrill D. Halling, Anita M. Orendt, Mark Strohmeier, Mark S. Solum, Vikki M. Tsefrikas, Toshikazu Hirao, Lawrence T. Scott, Ronald J. Pugmire and David M. Grant Phys. Chem. Chem. Phys., 2010, 12, 7934-7941 {{doi|10.1039/C001903H}}</ref> |
|
|
|
|
|
==Derivatives== |
|
== Derivatives == |
|
Sumanene derivatives <ref>''Bowl-to-bowl inversion of sumanene derivatives'' Toru Amaya, Hiroyuki Sakane, Toshiko Muneishi and Toshikazu Hirao Chem. Commun., 2008, 765-767 {{DOI|10.1039/B712839H}} </ref> such as ''naphtosumanene'' <ref>''Synthesis of Highly Strained π-Bowls from Sumanene'' Toru Amaya, Takuto Nakata and Toshikazu Hirao, Japan J. Am. Chem. Soc., 2009, 131 (31), pp 10810–10811 {{DOI|10.1021/ja9031693}}</ref> and ''trisialsumanene'' <ref>Communication Development of a Sila-Friedel−Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives Shunsuke Furukawa, Junji Kobayashi and Takayuki Kawashima J. Am. Chem. Soc., 2009, 131 (40), pp 14192–14193 {{DOI|10.1021/ja906566r}}</ref> <ref>''Synthesis, structures and optical properties of trisilasumanene and its related compounds'' Tomoharu Tanikawa, Masaichi Saito, Jing Dong Guo and Shigeru Nagase Org. Biomol. Chem., 2011, 9, 1731-1735 {{DOI|10.1039/C0OB00987C}}</ref> have been described. Chiral sumanenes are of some interest with respect to ] <ref>''Inherently chiral concave molecules—from synthesis to applications'' Agnieszka Szumna Chem. Soc. Rev., 2010, 39, 4274-4285 {{DOI|10.1039/B919527K}} </ref>, examples are chiral ''trimethylsumanene'' <ref>''Asymmetric Synthesis of a Chiral Buckybowl, Trimethylsumanene'' Shuhei Higashibayashi and Hidehiro Sakurai J. Am. Chem. Soc., 2008, 130 (27), pp 8592–8593 {{DOI|10.1021/ja802822k}}</ref> and a chiral sumanene cyclopentadienyl iron complex <ref>Sakane, H., Amaya, T., Moriuchi, T. and Hirao, T. (2009), A Chiral Concave-Bound Cyclopentadienyl Iron Complex of Sumanene. Angewandte Chemie International Edition, 48: 1640–1643. {{doi|10.1002/anie.200805567}}</ref> |
|
Sumanene derivatives <ref>''Bowl-to-bowl inversion of sumanene derivatives'' Toru Amaya, Hiroyuki Sakane, Toshiko Muneishi and Toshikazu Hirao Chem. Commun., 2008, 765-767 {{doi|10.1039/B712839H}}</ref> such as ''naphtosumanene'' <ref>''Synthesis of Highly Strained π-Bowls from Sumanene'' Toru Amaya, Takuto Nakata and Toshikazu Hirao, Japan J. Am. Chem. Soc., 2009, 131 (31), pp 10810–10811 {{doi|10.1021/ja9031693}}</ref> and ''trisialsumanene'' <ref>Communication Development of a Sila-Friedel−Crafts Reaction and Its Application to the Synthesis of Dibenzosilole Derivatives Shunsuke Furukawa, Junji Kobayashi and Takayuki Kawashima J. Am. Chem. Soc., 2009, 131 (40), pp 14192–14193 {{doi|10.1021/ja906566r}}</ref><ref>''Synthesis, structures and optical properties of trisilasumanene and its related compounds'' Tomoharu Tanikawa, Masaichi Saito, Jing Dong Guo and Shigeru Nagase Org. Biomol. Chem., 2011, 9, 1731-1735 {{doi|10.1039/C0OB00987C}}</ref> have been described. Chiral sumanenes are of some interest with respect to ],<ref>''Inherently chiral concave molecules—from synthesis to applications'' Agnieszka Szumna Chem. Soc. Rev., 2010, 39, 4274-4285 {{doi|10.1039/B919527K}}</ref> examples are chiral ''trimethylsumanene'' <ref>''Asymmetric Synthesis of a Chiral Buckybowl, Trimethylsumanene'' Shuhei Higashibayashi and Hidehiro Sakurai J. Am. Chem. Soc., 2008, 130 (27), pp 8592–8593 {{doi|10.1021/ja802822k}}</ref> and a chiral sumanene cyclopentadienyl iron complex <ref>Sakane, H., Amaya, T., Moriuchi, T. and Hirao, T. (2009), A Chiral Concave-Bound Cyclopentadienyl Iron Complex of Sumanene. Angewandte Chemie International Edition, 48: 1640–1643. {{doi|10.1002/anie.200805567}}</ref> |
|
|
|
|
|
== References == |
|
== References == |
|
{{Reflist}} |
|
{{Reflist}} |
|
|
{{polycyclic aromatic hydrocarbons}} |
|
|
|
|
] |
|
] |
|
] |
|
] |
|
|
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|