Royal Society of Chemistry, CrystEngComm, 22(17), p. 4205-4209
DOI: 10.1039/c5ce00600g
International Union of Crystallography, Acta Crystallographica Section A: Foundations and Advances, a1(71), p. s460-s460, 2015
DOI: 10.1107/s2053273315093201
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The host 2,2′-(benzene-1,4-diyl-diethynylene) diborneol has been employed to resolve racemic methylcyclohexanones and 2-butanol. For 2-methylcyclohexanone, the resultant inclusion compound yielded an enantiomeric excess of 72% (S) while with 3-methylcyclohexanone the enantiomeric excess was 57% (S). The host failed to resolve (R,S)– 2-butanol, and the inclusion compounds derived from the (R,S)–, (R)– and (S)– 2-butanol are isostructural, being dominated by a stable framework of host•••host hydrogen bonds. The non-templating effect of the 2-butanol was explained in terms of the secondary interactions occuring in these structures which were also analysed by the program CrystalExplorer.