Temperature-dependent racemic compound-conglomerate crystallization of 2,3:6,7-dibenzobicyclo[3.3.1]nona-2,6-diene-4,8-dione |
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| Institution: | 1. Institute of Physical Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland;2. Department of Chemistry, University of North Texas, Denton, 1155, Union, Circle, #305070, TX 76203-5017, USA;3. Faculty of Mathematics and Natural Sciences, School of Sciences, Cardinal Stefan Wyszynski University in Warsaw, Wóycickiego 1/3, 01-938 Warsaw, Poland;1. Medicinal & Natural Products Chemistry Research Center, Shiraz university of Medical Sciences, Shiraz, Iran;2. Department of Chemistry, Shiraz University, Shiraz 71946, Iran |
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| Abstract: | 2,3:6,7-dibenzobicyclo3.3.1]nona-2,6-diene-4,8-dione 1 is a new example of a compound capable of temperature-dependent racemate-conglomerate crystallization: at temperatures below 90°C crystals of the racemic compound (space group P1̄, Z=4) can be obtained, whereas above 100°C a conglomerate of (+)- and (−)-homochiral crystals (space group P212121, Z=4) forms and therefore it undergoes spontaneous resolution upon crystallization. Enantioselective analytical gas chromatography on a single crystal has been proposed as a simple method for detection of conglomerate formation. The 1H and 13C NMR spectra of 1 are analyzed in detail and the crystal structures of both species (racemic compound and single enantiomer) have been solved by X-ray structural analysis. |
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