Abstract
The structures of the title compounds, 1,2,4,7-tetra(carboxymethyl)cubane 1 and 1,2,3,5,7-penta(carboxymethyl)cubane2, have been determined.1 crystallized in the space group\(P\bar 1\) with cell dimensionsa=6.098(2),b=10.686(2),c=13.459(2) Å, α=69.82(1), β=77.01(1), γ=74.00(1)°, while2 crystallized in the monoclinic space group P21/c with cell dimensionsa=15.139(2),b=12.775(1),c=9.849(2) Å, β=107.01(1)°. These molecules were derived from their parent carboxylic acids by esterification with methanol. They are unusual for several reasons. The first is that they both contain substituents on adjacent carbon atoms in the cubane framework. There are only a few reports in the literature of this type of cubane structure. The second molecule is unique in that it has five substituents attached to a cubane moiety. This is the one of the few cubane derivatives with more than four substituents to be structurally characterized and results in a cubane molecule in which there are three faces with three substituents and three faces with only two substituents.
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The structures of pentanitrocubane and hexanitrocubane have recently been determined in this laboratory (presented at the 14th Annual Working Group Institute on the Synthesis of High Energy Density Materials, June 8, 1995). A manuscript is in preparation reporting the full details of these structures: P. Eaton, R. Gilardi, J. Li, and K. Lukin, to be published.
This structure was determined in 1964 and is based on only 97 independent structure amplitudes. Since this is an important benchmark molecule in cubane chemistry, it seems important that this structure should be repeated for a more accurate result.
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Butcher, R.J., Bashir-Hashemi, A. & Gilardi, R.D. The crystal and molecular structures of highly substituted cubanes: 1,2,4,7-tetra(carboxymethyl)cubane and 1,2,3,5,7-penta(carboxymethyl)cubane. J Chem Crystallogr 25, 661–670 (1995). https://doi.org/10.1007/BF01665973
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DOI: https://doi.org/10.1007/BF01665973