Chemistry:Anthracene–maleic anhydride adduct

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Anthracene–maleic anhydride adduct
Names
Systematic IUPAC name
(15S,19R)-17-oxapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2,4,6,9,11,13-hexaene-16,18-dione
Other names
  • 9,10-dihydroanthracene-9,10-endo-α,β-succinic anhydride[1]
  • endo-9,10-(α,β-Succinic anhydride)anthracene
  • 9,10-Ethanoanthracene-11,12-dicarboxylic anhydride
  • Dibenzobarallene
Identifiers
3D model (JSmol)
Properties
C18H12O3
Molar mass 276.291 g·mol−1
Appearance Colorless crystals
Melting point 262 °C (504 °F; 535 K)[2]
Structure
Monoclinic[3]
Cc[3]
a = 15.410 Å, b = 9.4020 Å, c = 11.0930 Å[3]
α = 90°, β = 124.235°, γ = 90°
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

The anthracene–maleic anhydride adduct is an organic compound and an example of a Diels–Alder adduct. It is commonly prepared in organic chemistry teaching laboratories as an example of the Diels–Alder reaction.[2][4]

Preparation

The anthracene–maleic anhydride adduct may be prepared by the reaction of equimolar amounts of anthracene and maleic anhydride in refluxing xylenes:[3]

Reaction scheme for Diels-Alder reaction of anthracene with maleic anhydride

The product crystallizes from the reaction mixture upon cooling.

Colorless crystals forming in a 100 mL roundbottom flask
Crystallization of anthracene–maleic anhydride adduct.

References

  1. ↑ "Anthracene-maleic anhydride Diels-Alder adduct" (in en). NIST Office of Data and Informatics. https://webbook.nist.gov/cgi/cbook.cgi?ID=C5443163. 
  2. ↑ 2.0 2.1 Jasperse, Craig. "Diels-Alder Reaction". https://web.mnstate.edu/jasperse/Chem365/Diels-Alder.pdf. 
  3. ↑ 3.0 3.1 3.2 3.3 Díaz de Delgado, Graciela; Ramírez V, Belkis; Velásquez, William; Rodríguez, Pedro (2002-05-15). "A new polymorph of 9,10-dihydroanthracene-9,10-α,β-succinic acid anhydride". Acta Crystallographica Section E: Structure Reports Online 58 (5): o501–o503. doi:10.1107/S1600536802005767. ISSN 1600-5368. Bibcode: 2002AcCrE..58O.501D. https://journals.iucr.org/paper?S1600536802005767. 
  4. ↑ Amin, Shikha; Barnes, Ashley; Buckner, Courtney; Jones, Jordan; Monroe, Mattie; Nurmomade, Leon; Pinto, Taylor; Starkey, Samuel et al. (2015-04-14). "Diels–Alder Reaction Using a Solar Irradiation Heat Source Designed for Undergraduate Organic Chemistry Laboratories". Journal of Chemical Education 92 (4): 767–770. doi:10.1021/ed500850c. ISSN 0021-9584. Bibcode: 2015JChEd..92..767A. https://pubs.acs.org/doi/10.1021/ed500850c. 



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