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2,3-Diethoxy-9,10-anthraquinone
Hassan Allouchi1, Georges Bravic, Nacer Lahrahar
1Laboratoire de Chimie Physique (PCMB EA 4246), Faculté de Pharmacie, Université de Tours, 31 avenue Monge, 37200 Tours, France. hassan.allouchi@univ-tours.fr
Acta Crystallographica. Section C, Crystal Structure Communications
|November 8, 2008
Summary
The crystal structure of 2,3-diethoxy-9,10-anthraquinone reveals unique molecular packing. This finding provides insight into the solvent-gelling properties of 2,3-disubstituted anthraquinones.
Area of Science:
- Organic Chemistry
- Crystallography
- Materials Science
Background:
- Anthraquinone derivatives are vital in dyes and pharmaceuticals.
- 2,3-disubstituted anthraquinones exhibit unexpected solvent-gelling capabilities.
- Molecular packing information for these gelling agents was previously unknown.
Purpose of the Study:
- To determine the crystal structure of a 2,3-disubstituted anthraquinone.
- To elucidate the molecular packing mode of 2,3-diethoxy-9,10-anthraquinone.
- To compare its packing with the parent 9,10-anthraquinone.
Main Methods:
- Single-crystal X-ray diffraction analysis was performed.
- The crystal structure of 2,3-diethoxy-9,10-anthraquinone was solved and refined.
- Structural comparison with 9,10-anthraquinone was conducted.
Main Results:
- The first X-ray structure of a 2,3-disubstituted anthraquinone, 2,3-diethoxy-9,10-anthraquinone (C18H16O4), is reported.
- A novel molecular packing arrangement was observed, with molecules on parallel crystallographic mirror planes.
- This packing differs significantly from the herring-bone arrangement in 9,10-anthraquinone.
Conclusions:
- The unique packing of 2,3-diethoxy-9,10-anthraquinone, with layers spaced at 3.4081 Å, resembles graphite.
- This structural insight may explain the solvent-gelling properties of these derivatives.
- The study establishes a structural basis for understanding the function of 2,3-disubstituted anthraquinones.
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