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9,10-Dihydroanthracene

January 01, 1970

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 as a hydrogen-donor.[2]

9,10-Dihydroanthracene
Names
Preferred IUPAC name
9,10-Dihydroanthracene
Identifiers
  • 613-31-0 Y
3D model (JSmol)
  • Interactive image
ChemSpider
  • 11446
ECHA InfoCard 100.009.398
  • 11940
UNII
  • Z142C238GB Y
  • DTXSID3075256
  • InChI=1S/C14H12/c1-2-6-12-10-14-8-4-3-7-13(14)9-11(12)5-1/h1-8H,9-10H2
    Key: WPDAVTSOEQEGMS-UHFFFAOYSA-N
  • c1ccc2c(c1)Cc3ccccc3C2
Properties
C14H12
Molar mass 180.250 g·mol−1
Appearance White solid
Density 1.19 g mL−1[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).

Preparation edit

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,[3] an application of the Bouveault–Blanc reduction. 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.

See also edit

References edit

  1. ^ Reboul, J. P.; Oddon, Y.; Caranoni, C.; Soyfer, J. C.; Barbe, J.; Pèpe, G. (1987). "Structure du Dihydro-9,10 Anthracène. Support Tricyclique de Médicaments Psychotropes". Acta Crystallographica Section C Crystal Structure Communications. 43 (3): 537–539. Bibcode:1987AcCrC..43..537R. doi:10.1107/S010827018709512X.
  2. ^ Collin, Gerd; Höke, Hartmut; Talbiersky, Jörg (2006). "Anthracene". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a02_343.pub2. ISBN 9783527303854.
  3. ^ Bass, K. C. (1962). "9,10-Dihydroanthracene". Organic Syntheses. 42: 48. doi:10.15227/orgsyn.042.0048.

January 01, 1970
dihydroanthracene, organic, compound, that, derived, from, polycyclic, aromatic, hydrocarbon, anthracene, several, isomers, dihydroanthracene, known, derivative, most, common, colourless, solid, that, used, carrier, hydrogen, donor, names, preferred, iupac, na. 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 as a hydrogen donor 2 9 10 Dihydroanthracene Names Preferred IUPAC name 9 10 Dihydroanthracene Identifiers CAS Number 613 31 0 Y 3D model JSmol Interactive image ChemSpider 11446 ECHA InfoCard 100 009 398 PubChem CID 11940 UNII Z142C238GB Y CompTox Dashboard EPA DTXSID3075256 InChI InChI 1S C14H12 c1 2 6 12 10 14 8 4 3 7 13 14 9 11 12 5 1 h1 8H 9 10H2Key WPDAVTSOEQEGMS UHFFFAOYSA N SMILES c1ccc2c c1 Cc3ccccc3C2 Properties Chemical formula C 14H 12 Molar mass 180 250 g mol 1 Appearance White solid Density 1 19 g mL 1 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 Infobox referencesPreparation editBecause 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 3 an application of the Bouveault Blanc reduction 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 See also editTriptycene analogue with three phenyl ringsReferences edit Reboul J P Oddon Y Caranoni C Soyfer J C Barbe J Pepe G 1987 Structure du Dihydro 9 10 Anthracene Support Tricyclique de Medicaments Psychotropes Acta Crystallographica Section C Crystal Structure Communications 43 3 537 539 Bibcode 1987AcCrC 43 537R doi 10 1107 S010827018709512X Collin Gerd Hoke Hartmut Talbiersky Jorg 2006 Anthracene Ullmann s Encyclopedia of Industrial Chemistry Weinheim Wiley VCH doi 10 1002 14356007 a02 343 pub2 ISBN 9783527303854 Bass K C 1962 9 10 Dihydroanthracene Organic Syntheses 42 48 doi 10 15227 orgsyn 042 0048 Retrieved from https en wikipedia org w index php title 9 10 Dihydroanthracene amp oldid 1220122358, wikipedia, wiki, book, books, library,

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