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

Abstract

Partial resolution of racemic methylcyclohexanones and 2-butanol via inclusion within a borneol dumb-bell host.

Crystal Inclusion Formation of a New Type of Dumbbell-Shaped Host Compound Featuring Two Bulky 2,3,4,5-Tetraphenylcyclopenta-2,4-dien-1-ol Terminal Groups Attached to a Linear Spacer Unit

“…As a matter of principle, this should be explained to the effect that the high sterical shielding of the host functional groups by the bulk of the pentacyclic building blocks prevents self-aggregation of the host molecules via conventional hydrogen bonding. Therefore, a secondary coordinating species of appropriate size (solvent molecule) is an essential prerequisite for the formation of an inclusion crystal corresponding with the basic idea of the coordinato-clathrate strategy, while the general structure of the molecules 1 – 4 meets the dumbbell shape construction principle − also favoring inclusion formation. Thus, both the hydrophobic nature of the host framework and the presence of a polar guest species determine the three-dimensional molecular assembly in the inclusion crystals formed of 1 – 4 .…”

“…This concept is commonly referred to as the “coordinato-clathrate” approach . Representative examples of host structures developed from this line of thought correspond to wheel-and-axle, , scissor-like, roof-shaped, or dumbbell type − molecular geometries.…”

Aspects of crystal engineering arising from packing behavior of functional mono para-substituted trityl compounds

“…34 In order to visualize quantitatively the different types of intermolecular interactions (hydrogen bonding, halogenbased interactions, C-H⋯π contacts, etc.) 34 In order to visualize quantitatively the different types of intermolecular interactions (hydrogen bonding, halogenbased interactions, C-H⋯π contacts, etc.)…”

“…Hirshfeld surfaces 17 represent an effective way to gain insight in the packing behavior of molecules in the crystalline state. 34 In order to visualize quantitatively the different types of intermolecular interactions (hydrogen bonding, halogenbased interactions, C-H⋯π contacts, etc.) two-dimensional fingerprint plots, 35 derived from Hirshfeld surfaces, were prepared by using the CrystalExplorer program (version 3.1).…”

Separation and Resolution of Methylcyclohexanones by Enclathration with Deoxycholic Acid

“…The host (2 S )-(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)­1,1-diphenylpropan-1-ol and its racemic (2RS) analogue yielded similar structures, and the resolution by the (2 S )-host was only partially successful . The host 2,2′-(benzene-1,4-diyl-diethynylene) diborneol resolved 2-methylcyclohexanone (2MCH e.e. 72% S) and 3-methylcyclohexanone (3MCH e.e.…”