9,10-Dihydroanthracene: Difference between revisions
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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]],<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> an application of the [[Bouveault–Blanc reduction]] developed by [[Louis Bouveault]] and Gustave Louis Blanc in 1903.<ref>{{cite journal|last1 = Bouveault|first1 = Louis|authorlink1=Louis Bouveault|last2 = Blanc|first2 = Gustave Louis|journal = [[Compt. Rend.]]|year = 1903|volume = 136|pages = 1676–1678|title = Préparation des alcools primaires au moyen des acides correspondants|language = French|trans-title = Preparation of primary alcohols by means of the corresponding acids|url = http://gallica.bnf.fr/ark:/12148/bpt6k3091c/f1676.image.langFR}}</ref><ref>{{cite journal|last1 = Bouveault|first1 = Louis|authorlink1=Louis Bouveault|last2 = Blanc|first2 = Gustave Louis|journal = [[Compt. Rend.]]|year = 1903|volume = 137|pages = 60–62|title = Préparation des alcools primaires au moyen des acides correspondants|language = French|trans-title = Preparation of primary alcohols by means of the corresponding acids}}</ref><ref>{{cite journal|last1 = Bouveault|first1 = Louis|authorlink1=Louis Bouveault|last2 = Blanc|first2 = Gustave Louis|journal = [[Bull. Soc. Chim. Fr.]]|year = 1904|volume = 31|pages = 666–672|title = Transformation des acides monobasiques saturés dans les alcools primaires correspondants|language = French|trans-title = Transforming saturated monobasic acids into the corresponding primary alcohols}}</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]]. |
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]],<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> an application of the [[Bouveault–Blanc reduction]] developed by [[Louis Bouveault]] and Gustave Louis Blanc in 1903.<ref>{{cite journal|last1 = Bouveault|first1 = Louis|authorlink1=Louis Bouveault|last2 = Blanc|first2 = Gustave Louis|journal = [[Compt. Rend.]]|year = 1903|volume = 136|pages = 1676–1678|title = Préparation des alcools primaires au moyen des acides correspondants|language = French|trans-title = Preparation of primary alcohols by means of the corresponding acids|url = http://gallica.bnf.fr/ark:/12148/bpt6k3091c/f1676.image.langFR}}</ref><ref>{{cite journal|last1 = Bouveault|first1 = Louis|authorlink1=Louis Bouveault|last2 = Blanc|first2 = Gustave Louis|journal = [[Compt. Rend.]]|year = 1903|volume = 137|pages = 60–62|title = Préparation des alcools primaires au moyen des acides correspondants|language = French|trans-title = Preparation of primary alcohols by means of the corresponding acids}}</ref><ref>{{cite journal|last1 = Bouveault|first1 = Louis|authorlink1=Louis Bouveault|last2 = Blanc|first2 = Gustave Louis|journal = [[Bull. Soc. Chim. Fr.]]|year = 1904|volume = 31|pages = 666–672|title = Transformation des acides monobasiques saturés dans les alcools primaires correspondants|language = French|trans-title = Transforming saturated monobasic acids into the corresponding primary alcohols|url = http://gallica.bnf.fr/ark:/12148/bpt6k5469971k/f670.image}}</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- carbon–hydrogen bonds are estimated at 78 kcal mol<sup>−1</sup>. Thus these bonds are about 20% weaker than typical C–H bonds. |
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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Revision as of 05:22, 1 August 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 | 180.250 g·mol−1 |
| Appearance | white solid |
| Density | 0.88 g mL−1 |
| 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,[2] an application of the Bouveault–Blanc reduction developed by Louis Bouveault and Gustave Louis Blanc in 1903.[3][4][5] 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.
- ^ Bouveault, Louis; Blanc, Gustave Louis (1903). "Préparation des alcools primaires au moyen des acides correspondants" [Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. (in French). 136: 1676–1678.
- ^ Bouveault, Louis; Blanc, Gustave Louis (1903). "Préparation des alcools primaires au moyen des acides correspondants" [Preparation of primary alcohols by means of the corresponding acids]. Compt. Rend. (in French). 137: 60–62.
- ^ Bouveault, Louis; Blanc, Gustave Louis (1904). "Transformation des acides monobasiques saturés dans les alcools primaires correspondants" [Transforming saturated monobasic acids into the corresponding primary alcohols]. Bull. Soc. Chim. Fr. (in French). 31: 666–672.