Issue 22, 2015

Inclusion compounds of a borneol dumb-bell host with methylcyclohexanones and 2-butanols: structures and resolutions

Abstract

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 occurring in these structures which were also analysed by the program CrystalExplorer.

Graphical abstract: Inclusion compounds of a borneol dumb-bell host with methylcyclohexanones and 2-butanols: structures and resolutions

Supplementary files

Article information

Article type
Paper
Submitted
26 Mar 2015
Accepted
25 Apr 2015
First published
27 Apr 2015

CrystEngComm, 2015,17, 4205-4209

Author version available

Inclusion compounds of a borneol dumb-bell host with methylcyclohexanones and 2-butanols: structures and resolutions

E. Batisai, L. R. Nassimbeni and E. Weber, CrystEngComm, 2015, 17, 4205 DOI: 10.1039/C5CE00600G

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