9,10-Dihydroanthracene: Difference between revisions
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'''9,10-Dihydroanthracene''' is an [[organic compound]] that is derived from the [[polycyclic aromatic hydrocarbon]] [[anthracene]]. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H<sub>2</sub> in various chemical reactions.<ref>Gerd Collin |
'''9,10-Dihydroanthracene''' is an [[organic compound]] that is derived from the [[polycyclic aromatic hydrocarbon]] [[anthracene]]. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H<sub>2</sub> in various chemical reactions.<ref>{{cite encyclopedia|first1 = Gerd|last1 = Collin|first2 = Hartmut|last2 = Höke|first3 = Jörg|last3 = Talbiersky|title = Anthracene|encyclopedia = [[Ullmann's Encyclopedia of Industrial Chemistry]]|publisher = [[Wiley-VCH]]|location = Weinheim|year= 2006|doi = 10.1002/14356007.a02_343.pub2}}</ref> |
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==Preparation== |
==Preparation== |
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Because the [[aromaticity]] is not compromised for the flanking rings, anthracene is susceptible to [[hydrogenation]] at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/[[ethanol]] under [[Bouveault–Blanc reduction]].<ref>K. C. Bass |
Because the [[aromaticity]] is not compromised for the flanking rings, anthracene is susceptible to [[hydrogenation]] at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/[[ethanol]] under [[Bouveault–Blanc reduction]].<ref>{{OrgSynth|first = K. C.|last = Bass|title = 9,10-Dihydroanthracene|year = 1962|volume = 42|pages = 48|doi = 10.15227/orgsyn.042.0048|prep = CV5P0398|collvol = 5|collvolpages = 398}}</ref> The reduction can be effected by magnesium as well. Finally, it can also be prepared by the coupling of [[benzyl chloride]] using [[aluminium chloride]] as a [[catalyst]]. |
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The [[bond dissociation energy]] for the 9- and 10- |
The [[bond dissociation energy]] for the 9- and 10- carbon–hydrogen bonds are estimated at 78 kcal mol<sup>−1</sup>. Thus these bonds are about 20% weaker than typical C–H bonds. |
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==References== |
==References== |
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Revision as of 16:22, 31 July 2017
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| Names | |
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| Preferred IUPAC name
9,10-Dihydroanthracene | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.009.398 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C14H12 | |
| Molar mass | 180.25 |
| Appearance | white solid |
| Density | 0.88 g/mL |
| Melting point | 108 to 109 °C (226 to 228 °F; 381 to 382 K) |
| Boiling point | 312 °C (594 °F; 585 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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9,10-Dihydroanthracene is an organic compound that is derived from the polycyclic aromatic hydrocarbon anthracene. Several isomers of dihydroanthracene are known, but the 9,10 derivative is most common. It is a colourless solid that is used as a carrier of H2 in various chemical reactions.[1]
Preparation
Because the aromaticity is not compromised for the flanking rings, anthracene is susceptible to hydrogenation at the 9- and 10- positions. It is produced in the laboratory by dissolving metal reduction using sodium/ethanol under Bouveault–Blanc reduction.[2] The reduction can be effected by magnesium as well. Finally, it can also be prepared by the coupling of benzyl chloride using aluminium chloride as a catalyst.
The bond dissociation energy for the 9- and 10- carbon–hydrogen bonds are estimated at 78 kcal mol−1. Thus these bonds are about 20% weaker than typical C–H bonds.
References
- ^ Collin, Gerd; Höke, Hartmut; Talbiersky, Jörg (2006). "Anthracene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_343.pub2.
- ^ Bass, K. C. (1962). "9,10-Dihydroanthracene". Organic Syntheses. 42: 48. doi:10.15227/orgsyn.042.0048; Collected Volumes, vol. 5, p. 398.